direct preparation of thiazoles, imidazoles, imidazopyridines and
TRANSCRIPT
Electronic supporting information
Direct preparation of thiazoles, imidazoles, imidazopyridines and thiazolidines from alkenes
Timothy J. Donohoe,*a Mikhail A Kabeshov,a Akshat Rathi, $a and Ian E. D. Smithb
1H and 13C NMR spectra of the isolated compounds Page 3a 2 3b 4 3c 6 3d 8 3e 10 3f 12 3g 14 3h 16 3i 18 3j 20 3k 22 3l 24 3m 26 3n 28 3o 30 5a 32 5b 34 5c 36 6a 38 6b 40 6c 42 6d 44 6e 46 7a 48 7b 50 7c 52 8a 54 8b 56 9 58
Page 1
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
28/02/2010 17:03:43
Formula C10
H10
N2S FW 190.2648
Acquisition Time (sec) 1.9923 Comment W150478 N14038-14-P2 mk772466 1H CDCl3 .. Kabeshov, Mikhail XDate 05 Jan 2010 22:06:56 Date Stamp 05 Jan 2010 22:06:56File Name D:\iodoketones\Suppl_data\N14038-14-P2\N14038-14-P2_010000fid Frequency (MHz) 400.13Nucleus 1H Number of Transients 16 Origin dpx400n Original Points Count 16384Owner chemist Points Count 16384 Pulse Sequence zg30 Receiver Gain 143.70SW(cyclical) (Hz) 8223.68 Solvent CHLOROFORM-d Spectrum Offset (Hz) 2456.4697Sweep Width (Hz) 8223.18 Temperature (degree C) 20.160
VerticalScaleFactor = 0.5
NS
CH3
NH2
N14038-14-P2_010000fid
8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0Chemical Shift (ppm)
0
0.05
0.10
0.15
0.20
0.25
0.30
0.35
0.40
0.45
0.50
Nor
mal
ized
Inte
nsity
3.041.951.042.032.00
2.39
5.287.29
7.30
7.32
7.38
7.40
7.42
7.55
7.57
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
28/02/2010 17:16:43
Formula C10
H10
N2S FW 190.2648
Acquisition Time (sec) 1.2517 Comment W150478 N14038-14-P2 mk772466 13C CDCl3 .. Kabeshov, Mikhail XDate 05 Jan 2010 23:47:12 Date Stamp 05 Jan 2010 23:47:12File Name D:\iodoketones\Suppl_data\N14038-14-P2\N14038-14-P2_012000fid Frequency (MHz) 100.62Nucleus 13C Number of Transients 2048 Origin dpx400n Original Points Count 32768Owner bruker Points Count 32768 Pulse Sequence zgdc30 Receiver Gain 2896.30SW(cyclical) (Hz) 26178.01 Solvent CHLOROFORM-d Spectrum Offset (Hz) 12023.3662 Sweep Width (Hz) 26177.21Temperature (degree C) 20.160
VerticalScaleFactor = 0.5
NS
CH3
NH2
N14038-14-P2_012000fid
184 176 168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8 0Chemical Shift (ppm)
0.05
0.10
0.15
0.20
0.25
0.30
0.35
0.40
0.45
0.50
Nor
mal
ized
Inte
nsity
12.3
3
76.6
877
.00
77.3
2
117.
41
127.
1312
8.19
128.
30
135.
06
145.
94163.
98
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
28/02/2010 17:25:52
Formula C11
H13
N3S FW 219.3060
Acquisition Time (sec) 1.9923 Comment W150494 N14038-16-P13 mk772466 1H CDCl3 .. Kabeshov, Mikhail XDate 07 Jan 2010 21:47:44 Date Stamp 07 Jan 2010 21:47:44File Name D:\iodoketones\Suppl_data\N14038-16-P13\N14038-16-P13_010000fid Frequency (MHz) 400.13Nucleus 1H Number of Transients 16 Origin dpx400n Original Points Count 16384Owner chemist Points Count 16384 Pulse Sequence zg30 Receiver Gain 574.70SW(cyclical) (Hz) 8223.68 Solvent CHLOROFORM-d Spectrum Offset (Hz) 2457.1042 Sweep Width (Hz) 8223.18Temperature (degree C) 21.160
VerticalScaleFactor = 0.5
N
NS
NH2
CH3
N14038-16-P13_010000fid
9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5Chemical Shift (ppm)
0
0.05
0.10
0.15
0.20
0.25
0.30
0.35
0.40
0.45
0.50
Nor
mal
ized
Inte
nsity
3.042.072.021.951.000.990.970.96
0.95
0.97
0.99
1.61
1.63
1.65
1.67
1.69
1.70
2.73
2.75
2.76
5.02
7.327.
337.34
7.357.
857.
878.54
8.55
8.78
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
28/02/2010 17:31:02
Formula C11
H13
N3S FW 219.3060
Acquisition Time (sec) 1.2517 Comment W150494 N14038-16-P13 mk772466 13C CDCl3 .. Kabeshov, Mikhail XDate 07 Jan 2010 23:25:52 Date Stamp 07 Jan 2010 23:25:52File Name D:\iodoketones\Suppl_data\N14038-16-P13\N14038-16-P13_012000fid Frequency (MHz) 100.62Nucleus 13C Number of Transients 2048 Origin dpx400n Original Points Count 32768Owner bruker Points Count 32768 Pulse Sequence zgdc30 Receiver Gain 6502.00SW(cyclical) (Hz) 26178.01 Solvent CHLOROFORM-d Spectrum Offset (Hz) 12027.3613 Sweep Width (Hz) 26177.21Temperature (degree C) 21.160
VerticalScaleFactor = 0.5
N
NS
NH2
CH3
N14038-16-P13_012000fid
240 220 200 180 160 140 120 100 80 60 40 20 0Chemical Shift (ppm)
0.05
0.10
0.15
0.20
0.25
0.30
0.35
0.40
0.45
0.50
Nor
mal
ized
Inte
nsity
13.7
3
25.4
029
.00
76.6
877
.00
77.3
2
123.
2512
6.10
131.
3313
5.79
142.
73
148.
2514
9.31
164.
46
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
28/02/2010 17:39:33
Formula C9H
8N
2S FW 176.2382
Acquisition Time (sec) 1.9923 Comment M68634 N14038-50-P12 mk772466 1H CDCl3 Kabeshov, Mikhail XDate 26 Feb 2010 10:48:32 Date Stamp 26 Feb 2010 10:48:32File Name D:\iodoketones\Suppl_data\N14038-50-P1\N14038-50-P1_010000fid Frequency (MHz) 400.13Nucleus 1H Number of Transients 16 Origin av400m Original Points Count 16384Owner root Points Count 16384 Pulse Sequence zg30 Receiver Gain 32.00SW(cyclical) (Hz) 8223.68 Solvent CHLOROFORM-d Spectrum Offset (Hz) 2465.5391Sweep Width (Hz) 8223.18 Temperature (degree C) 25.660
VerticalScaleFactor = 0.5
NS
NH2
N14038-50-P1_010000fid
8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5Chemical Shift (ppm)
0
0.05
0.10
0.15
0.20
0.25
0.30
0.35
0.40
0.45
0.50
Nor
mal
ized
Inte
nsity
2.030.971.002.012.00
5.24
6.73
7.28
7.30
7.37
7.39
7.41
7.77
7.79
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
28/02/2010 17:43:51
Formula C9H
8N
2S FW 176.2382
Acquisition Time (sec) 1.2517 Comment W150825 N14038-50-P1 mk772466 13C CDCl3 .. Kabeshov, Mikhail XDate 02 Feb 2010 20:35:12 Date Stamp 02 Feb 2010 20:35:12File Name D:\iodoketones\Suppl_data\N14038-50-P1\N14038-50-P1_012000fid Frequency (MHz) 100.62Nucleus 13C Number of Transients 2048 Origin dpx400n Original Points Count 32768Owner bruker Points Count 32768 Pulse Sequence zgdc30 Receiver Gain 14596.50SW(cyclical) (Hz) 26178.01 Solvent CHLOROFORM-d Spectrum Offset (Hz) 12028.1602 Sweep Width (Hz) 26177.21Temperature (degree C) 20.160
VerticalScaleFactor = 0.5
NS
NH2
N14038-50-P1_012000fid
192 184 176 168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8 0Chemical Shift (ppm)
0
0.05
0.10
0.15
0.20
Nor
mal
ized
Inte
nsity
102.
90
125.
9712
8.57
134.
62
151.
33
167.
08
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
28/02/2010 20:06:52
Formula C13
H18
N4S FW 262.3738
Acquisition Time (sec) 1.9923 Comment W151210 N14038-80-P13 mk772466 1H CDCl3 .. Kabeshov, Mikhail XDate 24 Feb 2010 18:57:04 Date Stamp 24 Feb 2010 18:57:04File Name D:\iodoketones\Suppl_data\N14038-80-P13\N14038-80-P13_010000fid Frequency (MHz) 400.13Nucleus 1H Number of Transients 16 Origin dpx400n Original Points Count 16384Owner chemist Points Count 16384 Pulse Sequence zg30 Receiver Gain 574.70SW(cyclical) (Hz) 8223.68 Solvent CHLOROFORM-d Spectrum Offset (Hz) 2457.2524 Sweep Width (Hz) 8223.18Temperature (degree C) 21.160
VerticalScaleFactor = 0.5
N
N
S
NH2
CH3
NCH3
CH3
N14038-80-P13_010000fid
10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0Chemical Shift (ppm)
0
0.05
0.10
0.15
0.20
0.25
0.30
0.35
0.40
0.45
0.50
Nor
mal
ized
Inte
nsity
3.172.082.096.151.951.051.001.00
0.94
0.96
0.98
1.591.
611.62
1.64
1.66
1.68
2.702.
722.
74
3.12
4.966.
556.
57
7.27
7.66
7.67
7.698.
308.
31
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
28/02/2010 20:09:54
Formula C13
H18
N4S FW 262.3738
Acquisition Time (sec) 1.2517 Comment W151210 N14038-80-P13 mk772466 13C CDCl3 .. Kabeshov, Mikhail XDate 24 Feb 2010 20:35:12 Date Stamp 24 Feb 2010 20:35:12File Name D:\iodoketones\Suppl_data\N14038-80-P13\N14038-80-P13_012000fid Frequency (MHz) 100.62Nucleus 13C Number of Transients 2048 Origin dpx400n Original Points Count 32768Owner bruker Points Count 32768 Pulse Sequence zgdc30 Receiver Gain 5160.60SW(cyclical) (Hz) 26178.01 Solvent CHLOROFORM-d Spectrum Offset (Hz) 12028.9590 Sweep Width (Hz) 26177.21Temperature (degree C) 21.160
VerticalScaleFactor = 0.5
N
N
S
NH2
CH3
NCH3
CH3
N14038-80-P13_012000fid
240 220 200 180 160 140 120 100 80 60 40 20 0Chemical Shift (ppm)
0
0.05
0.10
0.15
0.20
0.25
Nor
mal
ized
Inte
nsity
13.8
0
25.4
529
.13
38.1
9
105.
42
119.
3012
3.10
137.
51
147.
22
158.
24
164.
01
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
28/02/2010 18:12:06
Formula C9H
11N
3S
2FW 225.3337
Acquisition Time (sec) 1.9923 Comment W151000 N14038-64-P12 mk772466 1H CDCl3 .. Kabeshov, Mikhail XDate 12 Feb 2010 18:57:04 Date Stamp 12 Feb 2010 18:57:04File Name D:\iodoketones\Suppl_data\N14038-64-P12\N14038-64-P12_010000fid Frequency (MHz) 400.13Nucleus 1H Number of Transients 16 Origin dpx400n Original Points Count 16384Owner chemist Points Count 16384 Pulse Sequence zg30 Receiver Gain 143.70SW(cyclical) (Hz) 8223.68 Solvent CHLOROFORM-d Spectrum Offset (Hz) 2457.2446 Sweep Width (Hz) 8223.18Temperature (degree C) 20.160
VerticalScaleFactor = 0.5
NS
NS
CH3
NH2
N14038-64-P12_010000fid
10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5Chemical Shift (ppm)
0
0.05
0.10
0.15
0.20
0.25
0.30
0.35
0.40
0.45
0.50
Nor
mal
ized
Inte
nsity
3.102.102.082.051.000.98
0.99
1.01
1.03
1.63
1.65
1.66
1.68
1.70
1.72
2.77
2.79
2.81
5.37
8.01
8.73
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
28/02/2010 18:17:09
Formula C9H
11N
3S
2FW 225.3337
Acquisition Time (sec) 1.2517 Comment W151000 N14038-64-P12 mk772466 13C CDCl3 .. Kabeshov, Mikhail XDate 12 Feb 2010 20:35:12 Date Stamp 12 Feb 2010 20:35:12File Name D:\iodoketones\Suppl_data\N14038-64-P12\N14038-64-P12_012000fid Frequency (MHz) 100.62Nucleus 13C Number of Transients 2048 Origin dpx400n Original Points Count 32768Owner bruker Points Count 32768 Pulse Sequence zgdc30 Receiver Gain 9195.20SW(cyclical) (Hz) 26178.01 Solvent CHLOROFORM-d Spectrum Offset (Hz) 12023.3672 Sweep Width (Hz) 26177.21Temperature (degree C) 20.160
VerticalScaleFactor = 0.5
NS
NS
CH3
NH2
N14038-64-P12_012000fid
192 184 176 168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8Chemical Shift (ppm)
0
0.05
0.10
0.15
0.20
0.25
0.30
0.35
0.40
0.45
0.50
Nor
mal
ized
Inte
nsity
13.7
5
24.5
029.0
7
125.
45
133.
3213
6.35
140.
14
151.
76
164.
52
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
28/02/2010 19:59:57
Formula C11
H12
N2OS FW 220.2908
Acquisition Time (sec) 1.9923 Comment W151136 N14038-78-P12 mk772466 1H CDCl3 .. Kabeshov, Mikhail XDate 22 Feb 2010 22:06:56 Date Stamp 22 Feb 2010 22:06:56File Name D:\iodoketones\Suppl_data\N14038-78-P12\N14038-78-P12_010000fid Frequency (MHz) 400.13Nucleus 1H Number of Transients 16 Origin dpx400n Original Points Count 16384Owner chemist Points Count 16384 Pulse Sequence zg30 Receiver Gain 322.50SW(cyclical) (Hz) 8223.68 Solvent CHLOROFORM-d Spectrum Offset (Hz) 2457.3210 Sweep Width (Hz) 8223.18Temperature (degree C) 20.160
VerticalScaleFactor = 0.5
N S
NH2
OCH3
N14038-78-P12_010000fid
9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5Chemical Shift (ppm)
0
0.05
0.10
0.15
0.20
0.25
0.30
0.35
0.40
0.45
0.50
Nor
mal
ized
Inte
nsity
3.022.031.991.011.972.003.
39
4.49
5.31
7.33
7.35
7.377.
407.
427.
447.
577.
59
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
28/02/2010 19:59:13
Formula C11
H12
N2OS FW 220.2908
Acquisition Time (sec) 1.2517 Comment W151136 N14038-78-P12 mk772466 13C CDCl3 .. Kabeshov, Mikhail XDate 22 Feb 2010 23:45:04 Date Stamp 22 Feb 2010 23:45:04File Name D:\iodoketones\Suppl_data\N14038-78-P12\N14038-78-P12_012000fid Frequency (MHz) 100.62Nucleus 13C Number of Transients 2048 Origin dpx400n Original Points Count 32768Owner bruker Points Count 32768 Pulse Sequence zgdc30 Receiver Gain 7298.20SW(cyclical) (Hz) 26178.01 Solvent CHLOROFORM-d Spectrum Offset (Hz) 12026.5625 Sweep Width (Hz) 26177.21Temperature (degree C) 20.160
VerticalScaleFactor = 0.5
N S
NH2
OCH3
N14038-78-P12_012000fid
240 220 200 180 160 140 120 100 80 60 40 20 0Chemical Shift (ppm)
0
0.05
0.10
0.15
0.20
0.25
0.30
0.35
0.40
0.45
0.50
Nor
mal
ized
Inte
nsity
57.7
3
66.4
4
118.
97
127.
9012
8.34
128.
51
134.
51
149.
64166.
15
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0f1 (ppm)
-500
0
500
1000
1500
2000
2500
3000
3500
4000
4500
5000
5500
6000
3.08
0.99
1.01
0.98
1.01
1.00
0.00
2.67
3.34
3.35
3.35
3.35
3.36
4.70
6.84
7.48
7.50
7.52
7.88
7.90
7.95
8.35
8.35
8.36
S
N
NH2
CH3O
Parameter Value
1 Solvent MeOD
2 Pulse Sequence zg30
3 Acquisition Date 2010-11-18T21:55:59
4 Number of Scans 16
5 Spectrometer Frequency 400.13
6 Spectral Width 8278.1
7 Lowest Frequency -1660.1
8 Nucleus 1H
9 Acquired Size 32768
10 Spectral Size 65536
Page 14
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
0102030405060708090100110120130140150160170180190200210220230240250f1 (ppm)
0
2000
4000
6000
8000
10000
12000
14000
16000
18000
20000
22000
24000
26000
28000
30000
32000
3400027.0
3
48.5
148
.72
48.9
449
.15
49.3
649
.58
49.7
9
77.9
878
.31
78.6
3
103.
77
126.
6012
8.07
129.
6313
1.34
136.
0013
7.97
150.
11
170.
58
200.
24S
N
NH2
CH3O
Parameter Value
1 Solvent MeOD
2 Pulse Sequence zgpg30
3 Acquisition Date 2010-11-18T23:35:59
4 Number of Scans 2048
5 Spectrometer Frequency 100.62
6 Spectral Width 26178.0
7 Lowest Frequency -932.6
8 Nucleus 13C
9 Acquired Size 32768
10 Spectral Size 65536
Page 15
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.010.5f1 (ppm)
0
500
1000
1500
2000
2500
3000
1.95
1.98
1.98
1.00
2.49
2.50
2.50
2.50
2.51
3.32
7.10
7.23
7.24
7.25
7.26
7.27
7.78
7.80
7.81
8.52
8.53
S
N
NH2
N
Parameter Value
1 Solvent DMSO
2 Pulse Sequence zg30
3 Acquisition Date 2011-01-24T10:35:21
4 Number of Scans 16
5 Spectrometer Frequency 400.13
6 Spectral Width 8223.7
7 Lowest Frequency -1643.7
8 Nucleus 1H
9 Acquired Size 16384
10 Spectral Size 32768
Page 16
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
-100102030405060708090100110120130140150160170180190200210220230240250f1 (ppm)
-10000
0
10000
20000
30000
40000
50000
60000
70000
80000
90000
1E+05
1E+05
1E+05
1E+05
47.3
547
.56
47.7
847
.99
48.2
048
.42
48.6
3
106.
29
121.
2512
2.73
137.
76
148.
9414
9.92
152.
80
170.
24
N
SN
NH2
Parameter Value
1 Solvent MeOD
2 Pulse Sequence zgdc30
3 Acquisition Date 2010-08-25T22:52:55
4 Number of Scans 2048
5 Spectrometer Frequency 100.62
6 Spectral Width 26178.0
7 Lowest Frequency -1015.5
8 Nucleus 13C
9 Acquired Size 32768
10 Spectral Size 65536
Page 17
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.5f1 (ppm)
0
1000
2000
3000
4000
5000
6000
7000
8000
9000
10000
3.25
2.17
2.13
1.02
1.08
2.07
1.00
-0.0
0
1.40
1.41
1.43
4.38
4.39
4.41
4.43
5.20
6.82
7.43
7.45
7.47
7.95
7.96
7.96
7.98
8.42
8.42
8.43
SN
NH2
OO
CH3
Parameter Value
1 Solvent CDCl3
2 Pulse Sequence zg30
3 Acquisition Date 2010-08-23T18:04:13
4 Number of Scans 16
5 Spectrometer Frequency 400.13
6 Spectral Width 8223.7
7 Lowest Frequency -1640.9
8 Nucleus 1H
9 Acquired Size 16384
10 Spectral Size 32768
Page 18
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
-100102030405060708090100110120130140150160170180190200210220230240f1 (ppm)
-5000
0
5000
10000
15000
20000
25000
30000
35000
40000
45000
50000
55000
60000
65000
14.3
7
61.0
5
76.6
877
.00
77.3
2
103.
70
126.
9912
8.64
128.
6713
0.28
130.
8513
4.91
150.
33
166.
5516
7.37
SN
NH2
OO
CH3
Parameter Value
1 Solvent CDCl3
2 Pulse Sequence zgdc30
3 Acquisition Date 2010-08-23T19:42:57
4 Number of Scans 2048
5 Spectrometer Frequency 100.62
6 Spectral Width 26178.0
7 Lowest Frequency -1015.5
8 Nucleus 13C
9 Acquired Size 32768
10 Spectral Size 65536
Page 19
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.5f1 (ppm)
0
500
1000
1500
2000
2500
3000
3500
4000
4500
5000
2.94
1.93
1.03
4.00
2.49
2.50
2.50
2.50
2.51
3.34
3.85
7.16
7.25
7.91
7.92
7.92
7.94
7.94
7.96
7.96
7.97
SN
NH2
O
OCH3
Parameter Value
1 Solvent DMSO
2 Pulse Sequence zg30
3 Acquisition Date 2011-01-12T19:04:33
4 Number of Scans 16
5 Spectrometer Frequency 400.13
6 Spectral Width 8278.1
7 Lowest Frequency -1670.9
8 Nucleus 1H
9 Acquired Size 32768
10 Spectral Size 65536
Page 20
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
0102030405060708090100110120130140150160170180190200210f1 (ppm)
-1000
0
1000
2000
3000
4000
5000
6000
7000
8000
9000
10000
11000
12000
28.3
728
.56
28.7
528
.95
29.1
429
.33
29.5
2
51.3
4
104.
29
125.
6512
8.61
129.
54
139.
45
149.
67
166.
1416
8.24
205.
0520
5.26
205.
45
SN
NH2
O
OCH3
Parameter Value
1 Solvent Acetone
2 Pulse Sequence zgpg30
3 Acquisition Date 2010-11-30T20:45:34
4 Number of Scans 2048
5 Spectrometer Frequency 100.62
6 Spectral Width 26178.0
7 Lowest Frequency -1015.5
8 Nucleus 13C
9 Acquired Size 32768
10 Spectral Size 65536
Page 21
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.0f1 (ppm)
-1000
0
1000
2000
3000
4000
5000
6000
7000
8000
9000
10000
11000
12000
13000
14000
15000
16000
17000
18000
19000
20000
21000
3.11
2.00
0.93
3.10
0.98
0.00
2.39
2.44
5.18
6.45
7.18
7.19
7.20
7.21
7.22
7.51
7.51
7.52
7.53
SN
NH2
CH3Parameter Value
1 Solvent CDCl3
2 Pulse Sequence zg30
3 Acquisition Date 2010-08-23T21:14:21
4 Number of Scans 16
5 Spectrometer Frequency 400.13
6 Spectral Width 8223.7
7 Lowest Frequency -1660.1
8 Nucleus 1H
9 Acquired Size 16384
10 Spectral Size 32768
Page 22
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
-100102030405060708090100110120130140150160170180190200210220230240f1 (ppm)
-2000
0
2000
4000
6000
8000
10000
12000
14000
16000
18000
20000
22000
24000
26000
28000
30000
32000
34000
21.0
2
76.6
877
.00
77.3
2
105.
67
125.
7012
7.75
129.
5313
0.66
134.
8813
5.99
151.
32
166.
43
SN
NH2
CH3
Parameter Value
1 Solvent CDCl3
2 Pulse Sequence zgdc30
3 Acquisition Date 2010-08-23T22:53:14
4 Number of Scans 2048
5 Spectrometer Frequency 100.62
6 Spectral Width 26178.0
7 Lowest Frequency -1060.4
8 Nucleus 13C
9 Acquired Size 32768
10 Spectral Size 65536
Page 23
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0f1 (ppm)
-500
0
500
1000
1500
2000
2500
3000
3500
4000
4500
5000
5500
6000
3.02
1.03
2.00
1.85
2.00
2.49
2.50
2.50
2.50
2.51
3.34
3.76
6.82
6.90
6.93
7.01
7.70
7.71
7.72
7.73
O
SN
NH2
CH3
Parameter Value
1 Solvent DMSO
2 Pulse Sequence zg30
3 Acquisition Date 2011-01-19T19:05:17
4 Number of Scans 16
5 Spectrometer Frequency 400.13
6 Spectral Width 8278.1
7 Lowest Frequency -1670.9
8 Nucleus 1H
9 Acquired Size 32768
10 Spectral Size 65536
Page 24
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
0102030405060708090100110120130140150160170180190200210f1 (ppm)
-1000
0
1000
2000
3000
4000
5000
6000
7000
8000
9000
10000
1100038.8
839
.09
39.3
039
.51
39.7
239
.93
40.1
4
55.0
7
99.3
0
113.
79
126.
8012
7.84
149.
66
158.
49
168.
04
O
SN
NH2
CH3
Parameter Value
1 Solvent DMSO
2 Pulse Sequence zgpg30
3 Acquisition Date 2011-01-19T20:45:17
4 Number of Scans 2048
5 Spectrometer Frequency 100.62
6 Spectral Width 26178.0
7 Lowest Frequency -1061.3
8 Nucleus 13C
9 Acquired Size 32768
10 Spectral Size 65536
Page 25
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.010.5f1 (ppm)
-50
0
50
100
150
200
250
300
350
400
450
500
550
600
650
700
750
800
850
2.01
2.07
2.01
3.24
1.00
-0.0
0
2.83
2.83
2.85
2.86
2.87
3.01
3.03
3.05
5.01
7.12
7.13
7.14
7.15
7.16
7.16
7.17
7.18
7.22
7.26
7.67
7.69
S
N
NH2
Parameter Value
1 Solvent CDCl3
2 Pulse Sequence zg30
3 Acquisition Date 2010-11-10T19:05:58
4 Number of Scans 16
5 Spectrometer Frequency 400.13
6 Spectral Width 8278.1
7 Lowest Frequency -1677.3
8 Nucleus 1H
9 Acquired Size 32768
10 Spectral Size 65536
Page 26
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
0102030405060708090100110120130140150160170180190200f1 (ppm)
0
5000
10000
15000
20000
25000
30000
35000
40000
45000
21.0
7
28.4
7
38.8
839
.09
39.3
039
.51
39.7
239
.93
40.1
4
117.
52
122.
11
126.
18
131.
6613
4.23
144.
28
166.
56S
N
NH2Parameter Value
1 Solvent DMSO
2 Pulse Sequence zgpg30
3 Acquisition Date 2011-01-21T20:44:42
4 Number of Scans 2048
5 Spectrometer Frequency 100.62
6 Spectral Width 26178.0
7 Lowest Frequency -1060.2
8 Nucleus 13C
9 Acquired Size 32768
10 Spectral Size 65536
Page 27
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
23/03/2010 22:38:00
Formula C11
H20
N2S FW 212.3549
Acquisition Time (sec) 1.9923 Comment W151489 N14038-91-P12 mk772466 1H CDCl3 .. Kabeshov, Mikhail XDate 11 Mar 2010 22:06:56 Date Stamp 11 Mar 2010 22:06:56File Name G:\iodoketones\Suppl_data\N14038-91-P12\N14038-91-P12_010000fid Frequency (MHz) 400.13Nucleus 1H Number of Transients 16 Origin dpx400n Original Points Count 16384Owner chemist Points Count 16384 Pulse Sequence zg30 Receiver Gain 90.50SW(cyclical) (Hz) 8223.68 Solvent CHLOROFORM-d Spectrum Offset (Hz) 2457.2363 Sweep Width (Hz) 8223.18Temperature (degree C) 20.160
VerticalScaleFactor = 0.5
S
N
CH3
CH3
NH2
N14038-91-P12_010000fid
9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0Chemical Shift (ppm)
0
0.05
0.10
0.15
0.20
0.25
0.30
0.35
0.40
0.45
0.50
Nor
mal
ized
Inte
nsity
5.934.003.992.012.001.96
0.90
0.92
0.93
1.29
1.31
1.33
1.34
1.36
1.47
1.54
1.56
1.58
1.59
2.40
2.42
2.56
2.57
4.90
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
23/03/2010 22:42:02
Formula C11
H20
N2S FW 212.3549
Acquisition Time (sec) 1.2517 Comment W151489 N14038-91-P12 mk772466 13C CDCl3 .. Kabeshov, Mikhail XDate 11 Mar 2010 23:45:04 Date Stamp 11 Mar 2010 23:45:04File Name G:\iodoketones\Suppl_data\N14038-91-P12\N14038-91-P12_012000fid Frequency (MHz) 100.62Nucleus 13C Number of Transients 2048 Origin dpx400n Original Points Count 32768Owner bruker Points Count 32768 Pulse Sequence zgdc30 Receiver Gain 5792.60SW(cyclical) (Hz) 26178.01 Solvent CHLOROFORM-d Spectrum Offset (Hz) 12026.5625 Sweep Width (Hz) 26177.21Temperature (degree C) 20.160
VerticalScaleFactor = 0.5
S
N
CH3
CH3
NH2
N14038-91-P12_012000fid
192 184 176 168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8 0Chemical Shift (ppm)
0
0.05
0.10
0.15
0.20
0.25
0.30
0.35
0.40
0.45
0.50
Nor
mal
ized
Inte
nsity
13.8
313
.95
22.1
222
.52
28.7
331
.8234
.10
121.
88
147.
08
164.
03
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0f1 (ppm)
-100
0
100
200
300
400
500
600
700
800
900
1000
1100
1200
1300
1400
6.04
2.99
1.00
1.98
-0.0
0
1.19
1.21
2.13
3.04
3.05
3.07
3.09
3.10
7.26
CH3
SN
NH2
CH3CH3
Parameter Value
1 Solvent CDCl3
2 Pulse Sequence zg30
3 Acquisition Date 2010-11-08T15:43:59
4 Number of Scans 16
5 Spectrometer Frequency 400.13
6 Spectral Width 8223.7
7 Lowest Frequency -1648.5
8 Nucleus 1H
9 Acquired Size 16384
10 Spectral Size 32768
Page 30
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
-100102030405060708090100110120130140150160170180190200210220230240250f1 (ppm)
-2000
-1000
0
1000
2000
3000
4000
5000
6000
7000
8000
9000
10000
11000
12000
13000
14000
15000
16000
17000
18000
19000
20000
21000
14.6
2
24.8
527
.08
76.6
877
.00
77.3
2
129.
63
140.
30
163.
70
CH3
SN
NH2
CH3CH3
Parameter Value
1 Solvent CDCl3
2 Pulse Sequence zgpg30
3 Acquisition Date 2010-11-08T20:45:34
4 Number of Scans 2048
5 Spectrometer Frequency 100.62
6 Spectral Width 26178.0
7 Lowest Frequency -1017.2
8 Nucleus 13C
9 Acquired Size 32768
10 Spectral Size 65536
Page 31
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.010.511.011.512.0f1 (ppm)
-500
0
500
1000
1500
2000
2500
3000
3500
4000
4500
5000
5500
6000
6500
7000
7500
1.01
1.02
1.00
4.38
2.04
0.96
0.90
-0.0
0
6.41
6.43
6.72
6.98
7.18
7.27
7.29
7.81
7.83
7.83
8.25
8.26
10.1
5
SN
NH
N
Parameter Value
1 Solvent CDCl3
2 Pulse Sequence zg30
3 Acquisition Date 2010-06-02T17:55:08
4 Number of Scans 16
5 Spectrometer Frequency 400.13
6 Spectral Width 8223.7
7 Lowest Frequency -1688.5
8 Nucleus 1H
9 Acquired Size 16384
10 Spectral Size 32768
Page 32
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
0102030405060708090100110120130140150160170180190200210f1 (ppm)
-2000
-1000
0
1000
2000
3000
4000
5000
6000
7000
8000
9000
10000
11000
12000
13000
14000
15000
16000
17000
18000
19000
20000
21000
76.6
877
.00
77.3
2
105.
67
110.
58
116.
22
126.
1312
7.75
128.
70
134.
7213
7.44
146.
6214
9.31
151.
33
161.
07
SN
NH
N
Parameter Value
1 Solvent CDCl3
2 Pulse Sequence zgdc30
3 Acquisition Date 2010-06-02T19:33:56
4 Number of Scans 2048
5 Spectrometer Frequency 100.62
6 Spectral Width 26178.0
7 Lowest Frequency -1059.5
8 Nucleus 13C
9 Acquired Size 32768
10 Spectral Size 65536
Page 33
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
28/02/2010 20:18:43
Formula C14
H10
N2S FW 238.3076
Acquisition Time (sec) 1.9923 Comment W151226 N14038-81-P12 mk772466 1H CDCl3 .. Kabeshov, Mikhail XDate 25 Feb 2010 18:57:04 Date Stamp 25 Feb 2010 18:57:04File Name D:\iodoketones\Suppl_data\N14038-81-P12\N14038-81-P12_010000fid Frequency (MHz) 400.13Nucleus 1H Number of Transients 16 Origin dpx400n Original Points Count 16384Owner chemist Points Count 16384 Pulse Sequence zg30 Receiver Gain 322.50SW(cyclical) (Hz) 8223.68 Solvent CHLOROFORM-d Spectrum Offset (Hz) 2457.2410 Sweep Width (Hz) 8223.18Temperature (degree C) 21.160
VerticalScaleFactor = 0.5
N
S
N
N14038-81-P12_010000fid
10.5 10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0Chemical Shift (ppm)
0
0.05
0.10
0.15
0.20
0.25
0.30
0.35
0.40
0.45
0.50
Nor
mal
ized
Inte
nsity
4.251.022.081.001.000.97
7.37
7.38
7.41
7.45
7.47
7.55
8.00
8.02
8.33
8.358.
688.
68
9.26
9.26
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
28/02/2010 20:21:49
Formula C14
H10
N2S FW 238.3076
Acquisition Time (sec) 1.2517 Comment W151226 N14038-81-P12 mk772466 13C CDCl3 .. Kabeshov, Mikhail XDate 25 Feb 2010 20:35:12 Date Stamp 25 Feb 2010 20:35:12File Name D:\iodoketones\Suppl_data\N14038-81-P12\N14038-81-P12_012000fid Frequency (MHz) 100.62Nucleus 13C Number of Transients 2048 Origin dpx400n Original Points Count 32768Owner bruker Points Count 32768 Pulse Sequence zgdc30 Receiver Gain 9195.20SW(cyclical) (Hz) 26178.01 Solvent CHLOROFORM-d Spectrum Offset (Hz) 12024.9648 Sweep Width (Hz) 26177.21Temperature (degree C) 21.160
VerticalScaleFactor = 0.5
N
S
N
N14038-81-P12_012000fid
184 176 168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16Chemical Shift (ppm)
0.05
0.10
0.15
0.20
0.25
0.30
0.35
0.40
0.45
0.50
Nor
mal
ized
Inte
nsity
113.
23
123.
6812
6.41
128.
7812
9.67
133.
6213
4.03
147.
7215
0.77
156.
70
164.
30
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
28/02/2010 18:36:31
Formula C13
H15
NS FW 217.3299
Acquisition Time (sec) 1.9923 Comment W151001 N14038-65-P12 mk772466 1H CDCl3 .. Kabeshov, Mikhail XDate 12 Feb 2010 22:06:56 Date Stamp 12 Feb 2010 22:06:56File Name D:\iodoketones\Suppl_data\N14038-65-P12\N14038-65-P12_010000fid Frequency (MHz) 400.13Nucleus 1H Number of Transients 16 Origin dpx400n Original Points Count 16384Owner chemist Points Count 16384 Pulse Sequence zg30 Receiver Gain 203.20SW(cyclical) (Hz) 8223.68 Solvent CHLOROFORM-d Spectrum Offset (Hz) 2457.3210 Sweep Width (Hz) 8223.18Temperature (degree C) 20.160
VerticalScaleFactor = 0.5
N S
CH3CH3
CH3
N14038-65-P12_010000fid
11.0 10.5 10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5Chemical Shift (ppm)
0
0.05
0.10
0.15
0.20
0.25
0.30
0.35
0.40
0.45
0.50
Nor
mal
ized
Inte
nsity
9.301.982.022.00
1.51
7.307.
327.
347.
437.
457.93
7.95
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
28/02/2010 18:39:37
Formula C13
H15
NS FW 217.3299
Acquisition Time (sec) 1.2517 Comment W151001 N14038-65-P12 mk772466 13C CDCl3 .. Kabeshov, Mikhail XDate 12 Feb 2010 23:45:04 Date Stamp 12 Feb 2010 23:45:04File Name D:\iodoketones\Suppl_data\N14038-65-P12\N14038-65-P12_012000fid Frequency (MHz) 100.62Nucleus 13C Number of Transients 2048 Origin dpx400n Original Points Count 32768Owner bruker Points Count 32768 Pulse Sequence zgdc30 Receiver Gain 9195.20SW(cyclical) (Hz) 26178.01 Solvent CHLOROFORM-d Spectrum Offset (Hz) 12026.5625 Sweep Width (Hz) 26177.21Temperature (degree C) 20.160
VerticalScaleFactor = 0.5
N S
CH3CH3
CH3
N14038-65-P12_012000fid
230 220 210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30Chemical Shift (ppm)
0.05
0.10
0.15
0.20
0.25
0.30
0.35
0.40
0.45
0.50
Nor
mal
ized
Inte
nsity
30.9
2
37.7
9
111.
35
126.
3312
8.61
134.
92
154.
57
180.
88
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
28/02/2010 18:54:13
Formula C12
H14
N2
FW 186.2530
Acquisition Time (sec) 1.9923 Comment W151002 N14038-68-P12 mk772466 1H CDCl3 .. Kabeshov, Mikhail XDate 13 Feb 2010 01:16:48 Date Stamp 13 Feb 2010 01:16:48File Name D:\iodoketones\Suppl_data\N14038-68-P12\N14038-68-P12_010000fid Frequency (MHz) 400.13Nucleus 1H Number of Transients 16 Origin dpx400n Original Points Count 16384Owner chemist Points Count 16384 Pulse Sequence zg30 Receiver Gain 287.40SW(cyclical) (Hz) 8223.68 Solvent CHLOROFORM-d Spectrum Offset (Hz) 2456.9717 Sweep Width (Hz) 8223.18Temperature (degree C) 20.160
VerticalScaleFactor = 0.5
N NH
CH3
N14038-68-P12_010000fid
9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5Chemical Shift (ppm)
0
0.05
0.10
0.15
0.20
0.25
0.30
0.35
0.40
0.45
0.50
Nor
mal
ized
Inte
nsity
3.032.012.041.981.992.00
0.93
0.95
0.97
1.70
1.72
1.74
1.76
1.77
1.79
2.70
2.72
2.74
7.21
7.23
7.36
7.37
7.68
7.70
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
25/04/2010 12:36:57
Formula C12
H14
N2
FW 186.2530
Acquisition Time (sec) 1.0420 Comment DPX250 13C Acquisition Date 24 Apr 2010 08:19:12Date Stamp 24 Apr 2010 08:19:12 File Name G:\MK-GSK-250\MK-GSK-250_003000fidFrequency (MHz) 62.90 Nucleus 13C Number of Transients 30000 Origin dpx250Original Points Count 16384 Owner root Points Count 16384 Pulse Sequence zgpg30Receiver Gain 512.00 SW(cyclical) (Hz) 15723.27 Solvent CHLOROFORM-dSpectrum Offset (Hz) 6888.0454 Sweep Width (Hz) 15722.31 Temperature (degree C) 26.023
VerticalScaleFactor = 0.5
N NH
CH3
MK-GSK-250_003000fid
210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10Chemical Shift (ppm)
0
0.05
0.10
0.15
0.20
0.25
0.30
0.35
0.40
0.45
Nor
mal
ized
Inte
nsity
13.7
3
22.0
2
30.3
0
115.
13
124.
7512
6.78
128.
6713
2.56
137.
36
149.
39
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
28/02/2010 17:57:26
Formula C14
H11
N3
FW 221.2572
Acquisition Time (sec) 1.9923 Comment W151170 N14038-61-P13 mk772466 1H MeOD .. Kabeshov, Mikhail XDate 23 Feb 2010 22:43:12 Date Stamp 23 Feb 2010 22:43:12File Name D:\iodoketones\Suppl_data\N14038-61-P14\N14038-61-P14_010000fid Frequency (MHz) 400.13Nucleus 1H Number of Transients 16 Origin dpx400n Original Points Count 16384Owner chemist Points Count 16384 Pulse Sequence zg30 Receiver Gain 287.40SW(cyclical) (Hz) 8223.68 Solvent MeOD Spectrum Offset (Hz) 2463.0754 Sweep Width (Hz) 8223.18Temperature (degree C) 20.160
VerticalScaleFactor = 0.5
NNH
N
N14038-61-P14_010000fid
11.0 10.5 10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0Chemical Shift (ppm)
0
0.05
0.10
0.15
0.20
0.25
0.30
0.35
0.40
0.45
0.50
Nor
mal
ized
Inte
nsity
1.012.051.991.991.001.000.92
7.25
7.27
7.38
7.40
7.54
7.77
7.78
8.34
8.36
8.538.54
9.12
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
25/04/2010 12:19:37
Formula C14
H11
N3
FW 221.2572
Acquisition Time (sec) 1.1796 Comment DRX500 13C acquisition BBO probe Date 25 Apr 2010 08:36:16Date Stamp 25 Apr 2010 08:36:16 File Name G:\MK-GSK-500\MK-GSK-500_004000fidFrequency (MHz) 125.77 Nucleus 13C Number of Transients 25000 Origin drx500Original Points Count 32768 Owner root Points Count 32768 Pulse Sequence zgpg30Receiver Gain 32768.00 SW(cyclical) (Hz) 27777.78 Solvent CHLOROFORM-dSpectrum Offset (Hz) 12515.2432 Sweep Width (Hz) 27776.93 Temperature (degree C) 24.996
VerticalScaleFactor = 0.5
N NH
N
MK-GSK-500_004000fid
175 170 165 160 155 150 145 140 135 130 125 120 115 110 105 100 95 90 85 80 75Chemical Shift (ppm)
0.05
0.10
0.15
0.20
0.25
0.30
0.35
0.40
0.45
0.50
Nor
mal
ized
Inte
nsity
118.
42
124.
1712
5.04
126.
6112
7.38
128.
75
131.
76
134.
05
139.
36
143.
6714
5.61
148.
44
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
28/02/2010 19:40:56
Formula C11
H12
N2S FW 204.2914
Acquisition Time (sec) 1.9923 Comment W151133 N14038-77-P12 mk772466 1H CDCl3 .. Kabeshov, Mikhail XDate 22 Feb 2010 18:57:04 Date Stamp 22 Feb 2010 18:57:04File Name D:\iodoketones\Suppl_data\N14038-77-P12\N14038-77-P12_010000fid Frequency (MHz) 400.13Nucleus 1H Number of Transients 16 Origin dpx400n Original Points Count 16384Owner chemist Points Count 16384 Pulse Sequence zg30 Receiver Gain 287.40SW(cyclical) (Hz) 8223.68 Solvent CHLOROFORM-d Spectrum Offset (Hz) 2457.2043 Sweep Width (Hz) 8223.18Temperature (degree C) 20.160
VerticalScaleFactor = 0.5
NH N
S
CH3
N14038-77-P12_010000fid
10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5Chemical Shift (ppm)
0
0.05
0.10
0.15
0.20
0.25
0.30
0.35
0.40
0.45
Nor
mal
ized
Inte
nsity
3.042.011.403.032.00
1.29
1.31
1.33
3.02
3.03
3.05
3.07
7.24
7.25
7.27
7.36
7.37
7.39
7.69
7.71
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
25/04/2010 14:18:11
Formula C11
H12
N2S FW 204.2914
Acquisition Time (sec) 1.2517 Comment W152180 N14038-IM-1A mk772466 13C CDCl3 .. Kabeshov, Mikhail XDate 21 Apr 2010 20:03:12 Date Stamp 21 Apr 2010 20:03:12File Name G:\iodoketones\Suppl_data\N14038-77-P12\W152180_11\W152180_11_011000fid Frequency (MHz) 100.62Nucleus 13C Number of Transients 2048 Origin dpx400n Original Points Count 32768Owner chemist Points Count 32768 Pulse Sequence zgdc30 Receiver Gain 9195.20SW(cyclical) (Hz) 26178.01 Solvent CHLOROFORM-d Spectrum Offset (Hz) 12027.3613 Sweep Width (Hz) 26177.21Temperature (degree C) 22.160
VerticalScaleFactor = 0.5
N NH
S
CH3
W152180_11_011000fid
176 168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8Chemical Shift (ppm)
0
0.05
0.10
0.15
0.20
0.25
0.30
0.35
0.40
0.45
Nor
mal
ized
Inte
nsity
15.2
6
29.4
5
117.
61
124.
7612
7.10
128.
71
132.
25
139.
9314
0.63
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
28/02/2010 19:12:07
Formula C13
H14
N2
FW 198.2637
Acquisition Time (sec) 1.9923 Comment W151140 N14038-69-P13 mk772466 1H CDCl3 .. Kabeshov, Mikhail XDate 23 Feb 2010 04:26:40 Date Stamp 23 Feb 2010 04:26:40File Name D:\iodoketones\Suppl_data\N14038-69-P12\N14038-69-P12_010000fid Frequency (MHz) 400.13Nucleus 1H Number of Transients 16 Origin dpx400n Original Points Count 16384Owner chemist Points Count 16384 Pulse Sequence zg30 Receiver Gain 203.20SW(cyclical) (Hz) 8223.68 Solvent CHLOROFORM-d Spectrum Offset (Hz) 2457.2524 Sweep Width (Hz) 8223.18Temperature (degree C) 20.160
VerticalScaleFactor = 0.5
N N
N14038-69-P12_010000fid
9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5Chemical Shift (ppm)
0
0.05
0.10
0.15
0.20
0.25
0.30
0.35
0.40
0.45
0.50
Nor
mal
ized
Inte
nsity
4.222.052.081.000.982.012.00
1.95
1.97
1.98
1.99
2.00
2.92
2.94
2.953.96
3.98
3.99
7.07
7.19
7.21
7.33
7.35
7.37
7.74
7.75
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
28/02/2010 19:15:17
Formula C13
H14
N2
FW 198.2637
Acquisition Time (sec) 1.2517 Comment W151140 N14038-69-P13 mk772466 13C CDCl3 .. Kabeshov, Mikhail XDate 23 Feb 2010 06:06:56 Date Stamp 23 Feb 2010 06:06:56File Name D:\iodoketones\Suppl_data\N14038-69-P12\N14038-69-P12_012000fid Frequency (MHz) 100.62Nucleus 13C Number of Transients 2048 Origin dpx400n Original Points Count 32768Owner bruker Points Count 32768 Pulse Sequence zgdc30 Receiver Gain 3251.00SW(cyclical) (Hz) 26178.01 Solvent CHLOROFORM-d Spectrum Offset (Hz) 12024.9648 Sweep Width (Hz) 26177.21Temperature (degree C) 20.160
VerticalScaleFactor = 0.5
N N
N14038-69-P12_012000fid
160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8Chemical Shift (ppm)
0.05
0.10
0.15
0.20
0.25
0.30
0.35
0.40
0.45
0.50
Nor
mal
ized
Inte
nsity
21.1
323.0
124
.60
44.8
1
113.
80
124.
6012
6.37
128.
42
134.
40
140.
47
145.
18
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
23/03/2010 22:26:44
Formula C17
H16
N2O FW 264.3217
Acquisition Time (sec) 1.9923 Comment W151486 N14038-90-P12 mk772466 1H CDCl3 .. Kabeshov, Mikhail XDate 11 Mar 2010 18:57:04 Date Stamp 11 Mar 2010 18:57:04File Name G:\iodoketones\Suppl_data\N14038-90-P12\N14038-90-P12_010000fid Frequency (MHz) 400.13Nucleus 1H Number of Transients 16 Origin dpx400n Original Points Count 16384Owner chemist Points Count 16384 Pulse Sequence zg30 Receiver Gain 228.10SW(cyclical) (Hz) 8223.68 Solvent CHLOROFORM-d Spectrum Offset (Hz) 2457.2769 Sweep Width (Hz) 8223.18Temperature (degree C) 20.160
VerticalScaleFactor = 0.5
N
NH
OCH3
N14038-90-P12_010000fid
9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5Chemical Shift (ppm)
0
0.05
0.10
0.15
0.20
0.25
0.30
0.35
0.40
0.45
0.50
Nor
mal
ized
Inte
nsity
3.052.016.182.001.993.
41
4.57
7.27
7.317.
337.367.
387.41
7.60
7.61
7.86
7.88
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
25/04/2010 12:30:26
Formula C17
H16
N2O FW 264.3217
Acquisition Time (sec) 1.1796 Comment DRX500 13C acquisition BBO probe Date 24 Apr 2010 08:19:12Date Stamp 24 Apr 2010 08:19:12 File Name G:\MK-GSK-500\MK-GSK-500_002000fidFrequency (MHz) 125.77 Nucleus 13C Number of Transients 30000 Origin drx500Original Points Count 32768 Owner root Points Count 32768 Pulse Sequence zgpg30Receiver Gain 6502.00 SW(cyclical) (Hz) 27777.78 Solvent CHLOROFORM-dSpectrum Offset (Hz) 12513.5479 Sweep Width (Hz) 27776.93 Temperature (degree C) 24.996
VerticalScaleFactor = 0.5
N NH
OCH3
MK-GSK-500_002000fid
160 155 150 145 140 135 130 125 120 115 110 105 100 95 90 85 80 75 70 65 60 55 50Chemical Shift (ppm)
0.05
0.10
0.15
0.20
0.25
Nor
mal
ized
Inte
nsity
58.0
0
66.0
0
125.
5012
7.34
128.
6012
8.73
128.
8212
9.45
131.
74
135.
46
145.
94
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.010.511.0f1 (ppm)
-1000
0
1000
2000
3000
4000
5000
6000
7000
8000
9000
10000
11000
12000
13000
14000
0.99
1.00
1.01
2.03
0.99
1.00
1.99
1.02
6.77
6.78
6.80
7.16
7.18
7.44
7.64
7.86
7.95
7.97
7.97
8.11
8.13
NN
Parameter Value
1 Solvent CDCl3
2 Pulse Sequence zg30
3 Acquisition Date 2010-04-29T20:54:50
4 Number of Scans 16
5 Spectrometer Frequency 400.13
6 Spectral Width 8250.8
7 Lowest Frequency -1664.0
8 Nucleus 1H
9 Acquired Size 16384
10 Spectral Size 32768
Page 48
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
0102030405060708090100110120130140150160170180190200f1 (ppm)
0
20
40
60
80
100
120
140
160
180
200
220
240
260
280
300
320
340
360
380
76.6
877
.00
77.3
2
108.
09
112.
57
117.
44
124.
87
128.
7213
3.43
145.
51
NN
Parameter Value
1 Solvent CDCl3
2 Pulse Sequence zgdc30
3 Acquisition Date 2010-05-01T04:09:39
4 Number of Scans 2048
5 Spectrometer Frequency 100.62
6 Spectral Width 26246.7
7 Lowest Frequency -1093.2
8 Nucleus 13C
9 Acquired Size 32768
10 Spectral Size 65536
Page 49
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.010.511.011.512.012.5f1 (ppm)
0
500
1000
1500
2000
2500
3000
3500
4000
1.00
1.01
1.04
2.07
3.05
1.03
3.30
3.31
3.31
3.31
3.32
6.43
6.43
6.45
6.45
6.53
6.53
7.25
7.27
7.29
7.40
7.79
8.02
8.02
8.04
8.04
NN
NH2
Parameter Value
1 Solvent MeOD
2 Pulse Sequence zg30
3 Acquisition Date 2010-11-19T23:23:48
4 Number of Scans 16
5 Spectrometer Frequency 400.13
6 Spectral Width 8278.1
7 Lowest Frequency -1675.7
8 Nucleus 1H
9 Acquired Size 32768
10 Spectral Size 65536
Page 50
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
0102030405060708090100110120130140150160170180190200210f1 (ppm)
-5000
0
5000
10000
15000
20000
25000
30000
35000
40000
45000
50000
55000
60000
65000
70000
48.5
148
.72
48.9
449
.15
49.3
649
.58
49.7
9
93.6
6
108.
0910
8.35
126.
8012
7.91
128.
6512
9.76
135.
35
144.
97
149.
2314
9.90
NN
NH2
Parameter Value
1 Solvent MeOD
2 Pulse Sequence zgpg30
3 Acquisition Date 2010-11-20T01:03:48
4 Number of Scans 2048
5 Spectrometer Frequency 100.62
6 Spectral Width 26178.0
7 Lowest Frequency -858.4
8 Nucleus 13C
9 Acquired Size 32768
10 Spectral Size 65536
Page 51
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.010.5f1 (ppm)
0
500
1000
1500
2000
2500
3000
3500
4000
1.02
1.02
2.01
1.05
1.00
1.99
0.96
0.00
7.22
7.23
7.25
7.25
7.26
7.33
7.35
7.36
7.37
7.37
7.37
7.43
7.45
7.46
7.47
7.52
7.55
7.84
7.95
8.28
8.28
8.28
8.28
NN Br
Parameter Value
1 Solvent CDCl3
2 Pulse Sequence zg30
3 Acquisition Date 2010-11-20T02:29:36
4 Number of Scans 16
5 Spectrometer Frequency 400.13
6 Spectral Width 8278.1
7 Lowest Frequency -1676.1
8 Nucleus 1H
9 Acquired Size 32768
10 Spectral Size 65536
Page 52
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
0102030405060708090100110120130140150160170180190200f1 (ppm)
-500
0
500
1000
1500
2000
2500
3000
3500
4000
4500
5000
5500
6000
6500
7000
7500
8000
76.6
877
.00
77.3
2
106.
9710
8.25
118.
14
125.
5412
6.07
128.
7913
3.20
144.
1014
6.67
NN Br
Parameter Value
1 Solvent CDCl3
2 Pulse Sequence zgpg30
3 Acquisition Date 2010-11-20T04:09:38
4 Number of Scans 2048
5 Spectrometer Frequency 100.62
6 Spectral Width 26178.0
7 Lowest Frequency -1017.4
8 Nucleus 13C
9 Acquired Size 32768
10 Spectral Size 65536
Page 53
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0f1 (ppm)
0
500
1000
1500
2000
2500
3000
3500
4000
4500
5000
6.16
3.19
3.18
3.13
1.03
1.03
1.00
4.82
-0.0
0
1.18
1.19
1.24
1.27
1.28
1.45
1.47
1.58
2.28
3.04
3.06
3.07
3.72
3.73
3.75
5.50
7.20
7.20
7.21
7.24
7.26
7.30
7.31
7.32
7.33
7.34
SN
N
CH3
CH3
CH3
CH3
CH3
Parameter Value
1 Solvent CDCl3
2 Pulse Sequence zg30
3 Acquisition Date 2010-11-24T21:24:39
4 Number of Scans 16
5 Spectrometer Frequency 400.13
6 Spectral Width 8278.1
7 Lowest Frequency -1677.3
8 Nucleus 1H
9 Acquired Size 32768
10 Spectral Size 65536
Page 54
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
-100102030405060708090100110120130140150160170180190200210220230240250f1 (ppm)
-500
0
500
1000
1500
2000
2500
3000
3500
4000
4500
5000
5500
6000
6500
18.6
819
.51
19.8
123
.46
23.5
3
49.7
1
56.5
8
76.6
877
.00
77.3
2
93.4
8
125.
6212
8.99
130.
46
138.
1013
9.51
154.
19
SN
N
CH3
CH3
CH3
CH3
CH3
Parameter Value
1 Solvent CDCl3
2 Pulse Sequence zgpg30
3 Acquisition Date 2010-11-24T23:04:39
4 Number of Scans 2048
5 Spectrometer Frequency 100.62
6 Spectral Width 26178.0
7 Lowest Frequency -1016.9
8 Nucleus 13C
9 Acquired Size 32768
10 Spectral Size 65536
Page 55
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0f1 (ppm)
-200
0
200
400
600
800
1000
1200
1400
1600
1800
2000
2200
2400
2600
2800
3000
3200
3400
3600
3800
3.02
3.03
0.92
4.00
4.31
-0.0
0
2.27
3.13
5.71
7.00
7.01
7.03
7.05
7.06
7.06
7.22
7.24
7.24
7.26
7.27
7.29
7.31
7.35
7.35
7.37
7.38
Parameter Value
1 Solvent CDCl3
2 Pulse Sequence zg30
3 Acquisition Date 2010-10-18T18:05:47
4 Number of Scans 16
5 Spectrometer Frequency 400.13
6 Spectral Width 8278.1
7 Lowest Frequency -1678.9
8 Nucleus 1H
9 Acquired Size 32768
10 Spectral Size 65536
SN
N
F
CH3
CH3
Page 56
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
0102030405060708090100110120130140150160170180190200f1 (ppm)
-2000
-1000
0
1000
2000
3000
4000
5000
6000
7000
8000
9000
10000
11000
12000
13000
14000
15000
16000
17000
18000
19000
20000
21000
22000
23000
19.5
9
32.0
9
76.6
877
.00
77.3
2
94.6
3
115.
8811
6.10
122.
7112
2.79
126.
08
129.
6413
0.42
137.
8413
9.31
147.
87
157.
6816
0.07
160.
33S
N
N
F
CH3
CH3
Parameter Value
1 Solvent CDCl3
2 Pulse Sequence zgpg30
3 Acquisition Date 2010-10-15T21:11:47
4 Number of Scans 2048
5 Spectrometer Frequency 100.62
6 Spectral Width 26178.0
7 Lowest Frequency -1017.1
8 Nucleus 13C
9 Acquired Size 32768
10 Spectral Size 65536
Page 57
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
23/03/2010 22:11:42
Formula C16
H15
NO2
FW 253.2958
Acquisition Time (sec) 1.9923 Comment W151421 N14038-88-P12 mk772466 1H CDCl3 .. Kabeshov, Mikhail XDate 09 Mar 2010 20:20:16 Date Stamp 09 Mar 2010 20:20:16File Name G:\iodoketones\Suppl_data\N14038-88-P12\N14038-88-P12_010000fid Frequency (MHz) 400.13Nucleus 1H Number of Transients 16 Origin dpx400n Original Points Count 16384Owner chemist Points Count 16384 Pulse Sequence zg30 Receiver Gain 574.70SW(cyclical) (Hz) 8223.68 Solvent CHLOROFORM-d Spectrum Offset (Hz) 2457.3286 Sweep Width (Hz) 8223.18Temperature (degree C) 20.160
VerticalScaleFactor = 0.5
NH
O
CH3
OCH3
N14038-88-P12_010000fid
11.5 11.0 10.5 10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5Chemical Shift (ppm)
0
0.05
0.10
0.15
0.20
0.25
0.30
0.35
0.40
0.45
0.50
Nor
mal
ized
Inte
nsity
3.283.231.011.031.001.982.092.141.003.
873.
95
6.25
6.53
6.87
7.27
7.42
7.44
7.60
7.62
8.26
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
23/03/2010 22:18:24
Formula C16
H15
NO2
FW 253.2958
Acquisition Time (sec) 1.2517 Comment W151421 N14038-88-P12 mk772466 13C CDCl3 .. Kabeshov, Mikhail XDate 09 Mar 2010 22:00:32 Date Stamp 09 Mar 2010 22:00:32File Name G:\iodoketones\Suppl_data\N14038-88-P12\N14038-88-P12_012000fid Frequency (MHz) 100.62Nucleus 13C Number of Transients 2048 Origin dpx400n Original Points Count 32768Owner bruker Points Count 32768 Pulse Sequence zgdc30 Receiver Gain 9195.20SW(cyclical) (Hz) 26178.01 Solvent CHLOROFORM-d Spectrum Offset (Hz) 12027.3623 Sweep Width (Hz) 26177.21Temperature (degree C) 20.160
VerticalScaleFactor = 0.5
NH
O
CH3
OCH3
N14038-88-P12_012000fid
168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8Chemical Shift (ppm)
0
0.05
0.10
0.15
0.20
0.25
0.30
0.35
0.40
Nor
mal
ized
Inte
nsity
55.3
755
.67
86.7
2
91.9
2
97.1
3
114.
47
124.
4412
6.96
128.
95
132.
5113
5.06
138.
05
153.
67
157.
83
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011