Synthesis of 2-amino-5-arylthiazoles by palladium-catalyzed arylation at the C5 position with aryl iodides

Synlett

Volumn , Issue 19, 2007, Pages 2957-2960

  Priego, Julián ^a   Gutiérrez, Sonia ^a   Ferritto, Rafael ^a   Broughton, Howard B ^a  

^a ELI LILLY AND COMPANY   (Spain)

Author keywords

Catalysis; Cross coupling; Heck reaction; Heterocycles; Palladium

Indexed keywords

2 AMINO 5 ARYLTHIAZOLE DERIVATIVE; ARYL IODINE DERIVATIVE; IODINE DERIVATIVE; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PROTON; THIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; CATALYSIS; CHEMICAL BOND; CROSS COUPLING REACTION; HECK REACTION; SYNTHESIS;

EID: 37249069877     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-992368     Document Type: Article

References (48)

1. (a) Kalgutkar, A. S.; Crews, B. C.; Marnett, L. J. Biochem. 1996, 35, 9076.
2. (b) Dondoni, A. Comprehensive Chemistry II, Vol. 3; Shinkai, I., Ed.; Pergamon: Glasgow, 1996, 373.
3. (c) Hutchinson, I.; Stevens, M. F. G.; Westwell, A. D. Tetrahedron Lett. 2000, 41, 425.
4. (a) Schwander, H. In Ullman's Encyclopedia of Industrial Chemistry, Vol. A11; VCH: Weinheim, 1988, 279.
5. (b) Mori, A.; Sekiguchi, A.; Masui, K.; Shimada, T.; Horie, M.; Osakada, K.; Kawamoto, M.; Ikeda, T. J. Am. Chem. Soc. 2003, 125, 1700.
6. (a) Dölling, K.; Zaschke, H.; Schubert, H. J. Prakt. Chem. 1979, 321, 643.
7. (b) See also ref. 2b.
8. (a) Hassan, J.; Sévignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359.
9. (b) Anastasia, L.; Negishi, E. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley: New York, 2002, 311.
10. For recent reviews, see: (a) Dyker, G. Angew. Chem. Int. Ed. 1999, 38, 1698.
11. (b) Miura, M.; Nomura, M. Top. Curr. Chem. 2002, 219, 211.
12. (c) Wolfe, J. P.; Thomas, J. S. Curr. Org. Chem. 2005, 9, 625.
13. (a) Manolova, P.; Zhelyazkov, L.; Vodenicharov, R. Farmatsiya 1980, 30, 9.
14. (b) Volmajer, J.; Toplak, R.; Bittner, S.; Majcen Le Marechal, A. ARKIVOC 2003, (xiv), 49.
15. For Pd-catalyzed direct arylation of thiazoles, see: (a) Pivsa-Art, S.; Satoh, T.; Awamura, Y.; Miura, M.; Nomura, M. Bull. Chem. Soc. Jpn. 1998, 71, 467.
16. (b) Yokooji, A.; Okazawa, T.; Satoh, T.; Miura, M.; Nomura, M. Tetrahedron 2003, 59, 5685.
17. (c) Masui, K.; Mori, A.; Okano, K.; Takamura, K.; Kinoshita, M.; Ikeda, T. Org. Lett. 2004, 6, 2011.
18. (d) Parisien, M.; Valette, D.; Fagnou, K. J. Org. Chem. 2005, 70, 7578.
19. (e) Bellina, F.; Cauteruccio, S.; Rossi, R. Eur. J. Org. Chem. 2006, 1379. (f) See also ref. 2b.
20. For a recent review, see: Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174.
21. The Pd-coupling reaction with free 2-aminothiazole provided the corresponding amination product.
22. Lower yields were obtained with bidentate phosphine ligands, such as XantPhos (4,5-bis-diphenylphosphanyl-9,9-dimethyl-9H-xanthene, 64%), BINAP (60%) or DPPF [1,1′-bis(diphenylphosphino)ferrocene, 58%].
23. A similar effect was observed by Li et al. : Li, W.; Nelson, D. P.; Jensen, M. S.; Hoerrner, R. S.; Javadi, G. J.; Cai, D.; Larsen, R. D. Org. Lett. 2003, 5, 4835.
24. 3): δ = 163.91, 160.92, 135.83, 134.10, 129.81, 129.02, 127.62, 126.99, 59.99, 13.02.
25. (a) Grigg, R.; Sridharan, V.; Stevenson, P.; Sukirthalingam, S.; Worakum, T. Tetrahedron 1990, 46, 4003.
26. (b) Hughes, C. C.; Trauner, D. Angew. Chem. Int. Ed. 2002, 41, 1569.
27. (c) Lautens, M.; Fang, Y.-Q. Org. Lett. 2003, 5, 3679.
28. (d) Glover, B.; Harvey, K. A.; Liu, B.; Sharp, M. J.; Tymoschenko, M. Org. Lett. 2003, 5, 301.
29. (a) Catellani, M.; Chiusoli, G. P. J. Organomet. Chem. 1992, 425, 151.
30. (b) Martín-Matute, B.; Mateo, C.; Cárdenas, D. J.; Echavarren, A. M. Chem. Eur. J. 2001, 7, 2341.
31. (c) Lane, B. S.; Sames, D. Org. Lett. 2004, 6, 2897.
32. (d) Lane, B. S.; Brown, M. A.; Sames, D. J. Am. Chem. Soc. 2005, 127, 8050.
33. Park, C.-H.; Ryabova, V.; Seregin, I. V.; Sromek, A. W.; Gevorgyan, V. Org. Lett. 2004, 6, 1159.
34. Calculations were done using Maestro Version 7.5.112 and Jaguar Version 6.5, Schrödinger, LLC., Portland, Oregon: Vacek, G.; Perry, J. K.; Langlois, J.-M. Chem. Phys. Lett. 1999, 310, 189.
35. (a) Lee, C.; Parr, R. G.; Yang, W. Phys. Rev. 1988, 37, B785.
36. (b) Becke, A. D. J. Phys. Chem. 1993, 98, 5648.
37. (c) Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623.
38. García-Cuadrado, D.; Braga, A. A.; Maseras, F.; Echavarren, A. M. J. Am. Chem. Soc. 2006, 128, 1066.
39. A similar mechanism has also been recently proposed by Fagnou et al.: (a) Lafrance, M.; Rowley, C. N.; Woo, T. K.; Fagnou, K. J. Am. Chem. Soc. 2006, 128, 8754.
40. See also other recent examples: (b) Campeau, L.-C.; Parisien, M.; Leblanc, M.; Fagnou, K. J. Am. Chem. Soc. 2004, 126, 9186.
41. (c) Parisien, M.; Valette, D.; Fagnou, K. J. Org. Chem. 2005, 70, 7578.
42. (d) Campeau, L.-C.; Parisien, M.; Jean, A.; Fagnou, K. J. Am. Chem. Soc. 2006, 128, 581.
43. See kinetic isotope effects of C-H functionalization in: Hennessy, E. J.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 12084.
44. Recent DFT calculations in cross-coupling reactions: (a) Goossen, L. J.; Koley, D.; Hermann, H. L.; Thiel, W. J. Am. Chem. Soc. 2005, 127, 11102.
45. (b) Braga, A. A. C.; Morgon, N. H.; Ujaque, G.; Maseras, F. J. Am. Chem. Soc. 2005, 127, 9298.
46. (c) Mota, A. J.; Dedieu, A.; Bour, C.; Suffert, J. J. Am. Chem. Soc. 2005, 127, 7171.
47. Recent examples: (a) Pivsa-Art, S.; Satoh, T.; Awamura, Y.; Miura, M.; Nomura, M. Bull. Chem. Soc. Jpn. 1998, 71, 467.
48. (b) See also ref. 14c,d, 15.