chemical development, pharmaceutical development, … · regioselective synthesis of...
TRANSCRIPT
Regioselective Synthesis of 1,4-Disubstituted Imidazoles
Chemical Development, Pharmaceutical Development, R&D, Bristol-Myers Squibb Company, 1 Squibb
Drive, New Brunswick, New Jersey 08903
Table of Contents Copy of Spectra: S2
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
Regioselective Synthesis of 1,4-Disubstituted Imidazoles Page S2 / S16 Michael Schmidt* and Martin D. Eastgate
N
N
N
O
O
Br
22
1H NMR:
13C NMR:
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
Regioselective Synthesis of 1,4-Disubstituted Imidazoles Page S3 / S16 Michael Schmidt* and Martin D. Eastgate
N
N
N
O
O
OMe
24
1H NMR:
13C NMR:
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
Regioselective Synthesis of 1,4-Disubstituted Imidazoles Page S4 / S16 Michael Schmidt* and Martin D. Eastgate
N
N
N
O
O
CO2Et
26
1H NMR:
13C NMR:
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
Regioselective Synthesis of 1,4-Disubstituted Imidazoles Page S5 / S16 Michael Schmidt* and Martin D. Eastgate
1H NMR:
13C NMR:
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
Regioselective Synthesis of 1,4-Disubstituted Imidazoles Page S6 / S16 Michael Schmidt* and Martin D. Eastgate
1H NMR:
13C NMR:
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
Regioselective Synthesis of 1,4-Disubstituted Imidazoles Page S7 / S16 Michael Schmidt* and Martin D. Eastgate
N
N
N
N
O
O
32 1H NMR:
13C NMR:
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
Regioselective Synthesis of 1,4-Disubstituted Imidazoles Page S8 / S16 Michael Schmidt* and Martin D. Eastgate
N
N
N
O
O
HN
34 1H NMR:
13C NMR (with expansion):
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
Regioselective Synthesis of 1,4-Disubstituted Imidazoles Page S9 / S16 Michael Schmidt* and Martin D. Eastgate
1H NMR:
13C NMR:
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
Regioselective Synthesis of 1,4-Disubstituted Imidazoles Page S10 / S16 Michael Schmidt* and Martin D. Eastgate
1H NMR:
13C NMR:
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
Regioselective Synthesis of 1,4-Disubstituted Imidazoles Page S11 / S16 Michael Schmidt* and Martin D. Eastgate
Mixture of Enantiomers:
Compound (+)-38:
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
Regioselective Synthesis of 1,4-Disubstituted Imidazoles Page S12 / S16 Michael Schmidt* and Martin D. Eastgate
Compound (−)-38:
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
Regioselective Synthesis of 1,4-Disubstituted Imidazoles Page S13 / S16 Michael Schmidt* and Martin D. Eastgate
N
N
N
O
O
HO
(+)-40 1H NMR:
13C NMR:
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
Regioselective Synthesis of 1,4-Disubstituted Imidazoles Page S14 / S16 Michael Schmidt* and Martin D. Eastgate
N
N
N
O
O
HO
(+)-40
Mixture of Enantiomers:
Compound (+)-40:
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
Regioselective Synthesis of 1,4-Disubstituted Imidazoles Page S15 / S16 Michael Schmidt* and Martin D. Eastgate
N
N
N
O
O
HO
( )-40
Compound (−)-40:
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
Regioselective Synthesis of 1,4-Disubstituted Imidazoles Page S16 / S16 Michael Schmidt* and Martin D. Eastgate
1H NMR:
13C NMR:
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011