A facile synthetic approach to the preparation of 3-pyridyl derivatives: Preparations and coupling reactions of 3-pyridylzinc and its analogues

Synthesis

Volumn , Issue 22, 2009, Pages 3823-3827

  Kim, Seung Hoi ^a   Slocum, Tim B ^a   Rieke, Reuben D ^a  

^a Rieke Metals Incorporated   (United States)

Author keywords

3 pyridylzinc bromide; Coupling reaction; Heterocyclic derivatives

Indexed keywords

3-PYRIDYLZINC BROMIDE; CATALYTIC AMOUNTS; COUPLING REACTION; CROSS-COUPLING PRODUCTS; DIRECT PREPARATION; ELECTROPHILES; GOOD YIELD; LITHIUM CHLORIDE; ORGANOZINC REAGENTS; PYRIDYL; SYNTHETIC APPROACH;

CHLORINE COMPOUNDS; ORGANOMETALLICS; ZINC;

CHEMICAL REACTIONS;

3 BROMOPYRIDINE; 3 PYRIDYLZINC BROMIDE; 3 PYRIDYLZINC DERIVATIVE; BROMINE DERIVATIVE; LITHIUM CHLORIDE; PYRIDINE DERIVATIVE; REAGENT; UNCLASSIFIED DRUG; ZINC;

ARTICLE; CROSS COUPLING REACTION; REACTION ANALYSIS; SYNTHESIS;

EID: 73649127252     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1217000     Document Type: Article

References (35)

1. For recent examples, see: (a) Denton, T. T.; Zhang, X.; Cashman, J. R. J. Med. Chem. 2005, 48, 224.
2. (b) Davies, J. R.; Kane, P. D.; Moody, C. J.; Slawin, A. M. J. Org. Chem. 2005, 70, 5840.
3. (c) Yang, C-G.; Huang, H.; Jiang, B. Curr. Org. Chem. 2004, 8, 1691.
4. (d) Che, D.; Wegge, T.; Stubbs, M. T.; Seitz, G.; Meier, H.; Methfessel, C. J. Med. Chem. 2001, 44, 47.
5. (a) Trecourt, F.; Gervais, B.; Mallet, M.; Queguiner, G. J. Org. Chem. 1996, 61, 1673.
6. (b) Trecourt, F.; Gervais, B.; Mongin, O.; Le Gal, C.; Mongin, F.; Queguiner, G. J. Org. Chem. 1998, 63, 2892.
7. (a) Hargreaves, S. L.; Pilkington, B. L.; Russell, S. E.; Worthington, P. A. Tetrahedron Lett. 2000, 41, 1653.
8. (b) Zimmermann, J.; Buchdunger, E.; Mett, H.; Meyer, T.; Lydon, N. B. Bioorg. Med. Chem. Lett. 1997, 7, 187.
9. (c) Zimmermann, J.; Buchdunger, E.; Mett, H.; Meyer, T.; Lydon, N. B. Bioorg. Med. Chem. Lett. 1996, 6, 1221.
10. Getmanenko, Y. A.; Twieg, R. J. J. Org. Chem. 2008, 73, 830.
11. (a) Furukawa, N.; Shibutani, T.; Fujihara, H. Tetrahedron Lett. 1987, 28, 5845.
12. (b) Berillon, L.; Lepretre, A.; Turck, A.; Ple, N.; Queguiner, G.; Cahiez, G.; Knöchel, P. Synlett 1998, 1359.
13. (c) Trecourt, F.; Breton, G.; Mongin, F.; Marsais, F.; Queguiner, G. Tetrahedron Lett. 1999, 40, 4339.
14. (d) Abarbri, M.; Dehmel, F.; Knochel, P. Tetrahedron Lett. 1999, 40, 7449.
15. (e) Abarbri, M.; Thibonnet, J.; Berillon, L.; Dehmel, F.; Rottlander, M.; Knöchel, P. J. Org. Chem. 2000, 65, 4618.
16. (f) Trecourt, F.; Breton, G.; Bonnet, V.; Mongin, F.; Marsais, F.; Queguiner, G. Tetrahedron 2000, 56, 1349.
17. (g) Dumouchel, S.; Mongin, F.; Trecourt, F.; Queguiner, G. Tetrahedron Lett. 2003, 44, 3887.
18. Simkovsky, N. M.; Ermann, M.; Roberts, S. M.; Parry, D. M.; Baxter, A. D. J. Chem. Soc., Perkin Trans. 1 2002, 1847.
19. (a) Font-Sanchis, E.; Cespedes-Guirao, F. J.; Sastre-Santos, A.; Fernandez-Lazaro, F. J. Org. Chem 2007, 72, 3589.
20. (b) Lee, P. H.; Seomoon, D.; Lee, K. Org. Lett. 2005, 7, 343.
21. (c) Chen, Y.-H.; Knochel, P. Angew. Chem. Int. Ed. 2008, 47, 7648.
22. (a) Molander, G. A.; Canturk, B.; Kennedy, L. E. J. Org. Chem. 2009, 74, 973.
23. (b) Billingsley, K.; Buchwald, S. L. J. Am. Chem. Soc. 2007, 129, 3358.
24. (c) Thompson, A. E.; Hughes, G.; Batsanov, A. S.; Bryce, M. R.; Parry, P. R.; Tarbit, B. J. Org. Chem. 2005, 70, 388.
25. (d) Li, W.; Nelson, D. P.; Jensen, M. S.; Hoerrner, R. S.; Cai, D.; Larsen, R. D.; Reider, P. J. J. Org. Chem 2002, 67, 5394.
26. (e) Cai, D.; Larsen, R. D.; Reider, P. J. Tetrahedron Lett. 2002, 43, 4285.
27. For the side reaction of lithiation of 3-halopyridines, see: Mallet, M.; Branger, G.; Marsais, F.; Queguiner, G. J. Organomet. Chem. 1990, 382, 319; see also references 5c and 5f.
28. (a) Sakamoto, T.; Kondo, Y.; Murata, N.; Yamanaka, H. Tetrahedron 1993, 49, 9713.
29. (b) Sakamoto, T.; Kondo, Y.; Murata, N.; Yamanaka, H. Tetrahedron Lett. 1992, 33, 5373.
30. (c) Pryor, L.; Kiessling, A. Am. J. Undergraduate Res. 2002, 1, 25.
31. (d) Bell, A. S.; Roberts, D. A.; Ruddock, K. S. Synthesis 1987, 843.
32. (e) Sugimoto, O.; Yamada, S.; Tanji, K. J. Org. Chem. 2003, 68, 2054.
33. (f) Sugimoto, O.; Yamada, S.; Tanji, K. Tetrahedron Lett. 2002, 43, 3355.
34. Rieke, R. D. Science 1989, 246, 1260.
35. Krasovskiy, A.; Malakhov, V.; Gavryushin, A.; Knochel, P. Angew. Chem. Int. Ed. 2006, 45, 6040.