Regioselective synthesis of 1-aklyl-4-(3-pyridyl)-substituted imidazole

Organic Process Research and Development

Volumn 8, Issue 6, 2004, Pages 955-957

  Wei, Hengxu ^a   Sudini, Ravinder ^a   Yin, Hao ^a  

^a GLAXOSMITHKLINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL GROUP; BORONIC ACID DERIVATIVE; BROMINE; IMIDAZOLE;

ARTICLE; BROMINATION; CHEMICAL REACTION; DRUG SYNTHESIS; STEREOCHEMISTRY; SUZUKI REACTION;

EID: 10044254546     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op0498767     Document Type: Article

References (22)

1. (a) Agouridas, C.; Denis, A.; Auger, J.-M.; Benedetti, Y.; Bonnefoy, A.; Bretin, F.; Chantot, J.-F.; Dussarat, A.; Fromentin, C.; Gouin D'Ambrières, S.; Lachaud, S.; Laurin, P.; Le Martret, O.; Loyau, V.; Tessot, N. J. Med. Chem. 1998, 41, 4080-4100.
2. (b) Denis, A.; Bretin, F.; Fromentin, C.; Bonnet, A.; Piltan, G.; Bonnefoy, A.; Agouridas, C. Bioorg. Med. Chem. Lett. 2000, 10, 2019-2022.
3. (a) Denis, A.; Agouridas, C.; Auger, J. M.; Benedetti, Y.; Bonnefoy, A.; Bretin, F.; Chantot, J. F.; Dussarat, A.; Fromentin, C.; D'Ambrieres, S. G.; Lachaud, S.; Laurin, P.; Martret, O. L.; Loyau, V.; Tessot, N.; Pejac, J. M.; Perron, S. Bioorg. Med. Chem. Lett. 1999, 9, 3075-3080.
4. (b) Ripin, D. H. B.; Vanderplas, B. C.; Kaneko, T.; McMillen, W. T.; McLaughlin, R. W. (Pfizer Inc) U.S. Patent 6,403,776, 2002.
5. (c) Chu, D.; Burger, M.; Lin, X.; Georgia Law, C.; Plattner, J.; Rico, A. (Chiron Corp.) WO 2003004509.
6. (d) Dominique, L.; Gilles, D. R.; Franck, H.; Didier, B.; Thomas, R. (Aventis Pharma S.A.) WO 2004022544.
7. (e) Suleman, A.; Andrea, B.; Francesca, C.; Antun, H.; Gorjana, L.; Sergio, L.; Zorica, M. I.; Stjepan, M.; Alfonso, P.; Marko, D. (GlaxoSmithKline Plc) WO 2002032917.
8. Kirchhoff, E. W.; Anderson, D. R.; Zhang, S.; Cassidy, C. S.; Flavin, M. T. Org. Process Res. Dev. 2001, 5, 50-53.
9. (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483.
10. (b) Suzuki, A. J. Organomet. Chem. 1999, 576, 147-168.
11. (c) Stanforth, S. P. Tetrahedron 1998, 54, 263-303. Kotha, S.; Lahiri, K.; Kashinath, D. Tetrahedron 2002, 58, 9633-9695.
12. (c) Stanforth, S. P. Tetrahedron 1998, 54, 263-303. Kotha, S.; Lahiri, K.; Kashinath, D. Tetrahedron 2002, 58, 9633-9695.
13. Li, J. J.; Gribble, G. W. Palladium in Heterocyclic Chemistry; Pergamon: Oxford, 2000.
14. Miyaura, N.; Yamada, K.; Suginome, H.; Suzuki, A. J. Am. Chem. Soc. 1985, 107, 972-980.
15. Iddon, B.; Khan, N. J. Chem. Soc., Perkin Trans. 1 1987, 1453-1455.
16. Lipton, M. F.; Mauragis, M. A.; Maloney, M. T.; Veley, M. F.; VanderBor, D. W.; Newby, J. J.; Appell, R. B.; Daugs, E. D. Org. Process Res. Dev. 2003, 7, 385-392.
17. (a) Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 1998, 37, 3387-3388.
18. (b) Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020-4028.
19. (c) Zapf, A.; Ehrentraut, A.; Beller, M. Angew. Chem., Int. Ed. 2000, 39, 4153-4155.
20. Fischer, F. C.; Havinga, E. Recl. Trav. Chim. Pays-Bas 1974, 93, 21-24.
21. (a) Parrish, J. P.; Floyd, R. J.; Jung, K. W. Abstracts of Papers, 223rd ACS National Meeting, Orlando, FL, United States, April 7-11, 2002.
22. (b) Smith, K. A.; Campi, E. M.; Jackson, W. R.; Marcuccio, S.; Naeslund, C. G. M.; Deacon, G. B. Synlett 1997, 131-132.