Concise and Efficient Synthesis of 4-Fluoro-1H-pyrrolo[2,3-b]pyridine

Organic Letters

Volumn 5, Issue 26, 2003, Pages 5023-5025

  Thibault, Carl ^a   L'Heureux, Alexandre ^a   Bhide, Rajeev S ^b   Ruel, Réjean ^a  

^a BRISTOL MYERS SQUIBB   (United States)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

1H PYRROLO[2,3 B]PYRIDINE N OXIDE; 4 FLUORO 1H PYRROLE[2,3 B]PYRIDINE; HALOGEN; LITHIUM; OXIDE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; FLUORINATION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0346025404     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol036030z     Document Type: Article

References (34)

1. Mérour, J. Y.; Joseph, B. Curr. Org. Chem. 2001, 5, 471 and references cited therein.
2. (a) Balz, G.; Schiemann, G. Ber. 1927, 60, 1186.
3. (b) Milner, J. D. Synth. Commun. 1992, 22 (1), 73.
4. (c) Laali, K. K.; Gettwert, V. J. J. Fluorine Chem. 2001, 107, 31.
5. Reviews: (a) Roe, A. Org. React. 1949, 5, 193. (b) Suschitzky, H. Adv. Fluorine Chem. 1965, 4, 1.
6. Reviews: (a) Roe, A. Org. React. 1949, 5, 193. (b) Suschitzky, H. Adv. Fluorine Chem. 1965, 4, 1.
7. For recent reviews: (a) Taylor, S. D.; Kotoris, C. C.; Hum, G. Tetrahedron 1999, 55, 12431. (b) Lal, G. S.; Pez, G. P.; Syvret, R. G. Chem. Rev. 1996, 96, 1737 and references cited therein.
8. For recent reviews: (a) Taylor, S. D.; Kotoris, C. C.; Hum, G. Tetrahedron 1999, 55, 12431. (b) Lal, G. S.; Pez, G. P.; Syvret, R. G. Chem. Rev. 1996, 96, 1737 and references cited therein.
9. (a) Meade, E. A.; Beauchamp, L. M. J. Heterocycl. Chem. 1996, 33, 303.
10. (b) Antonini, I.; Claudi, F.; Cristalli, G.; Franchetti, P.; Grifantini, M.; Martelli, S. J. Med. Chem. 1982, 25, 1258.
11. (c) Schneller, S. W.; Luo, J.-K. J. Org. Chem. 1980, 45, 4045.
12. Benoît, S.; Gingras, S. Processes for the preparation of antiviral 7-azaindole derivatives. U.S. Provisional Patent 60/367,401, 2003.
13. Girgis, N. S.; Larson, S. B.; Robins, R. K.; Cottam, H. B. J. Heterocycl. Chem. 1989, 26, 317.
14. Wolfe, J. P.; Tomori, H.; Sadighi, J. P.; Yin, J.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1158.
15. (a) Jaime-Figueroa, S.; Liu, Y.; Muchowski, J. M.; Putman, D. G. Tetrahetron Lett. 1998, 39, 1313.
16. Other deallylation conditions attempted did not improve yield; see other conditions in ref 9a and: (b) Garro-Helion, F.; Merzouk, A.; Guibé, F. J. Org. Chem. 1993, 58, 6109.
17. On a larger scale, purification could also be done using Dowex 50W X 4 resin.
18. (a) Clark, R. D.; Berger, J.; Garg, P.; Weinhardt, K. K.; Speeding, M.; Kilpatrick, A. T.; Brown, C. M.; MacKinnon, A. C. J. Med. Chem. 1990, 33, 591.
19. (b) Mirsadeghi, S.; Prasad, G. K. B.; Whittaker, N.; Thakker, D. R. J. Org. Chem. 1989, 54, 3091.
20. Hannah, J.; Johnson, C. R.; Wagner, A. F.; Walton, E. J. Med. Chem. 1982, 25, 457.
21. Vlasov, V. M. J. Fluorine Chem. 1993, 61, 193.
22. (a) Aksenov, V. V.; Vlasov, V. M.; Moryakina, I. M.; Rodionov, P. P.; Fadeeva, V. P.; Chertok, V. S.; Yakobson, G. G. J. Fluorine Chem. 1985, 28, 73.
23. (b) Starks, C. M.; Liotta, C. Phase Transfer Catalysis; Academic Press: New York; 1978.
24. Block, E.; Aslam, M.; Eswarakrishnan, V.; Gebreyes, K.; Hutchinson, J.; Iyer, R.; Laffitte, J.-A.; Wall, A. J. Am. Chem. Soc. 1986, 108, 4568.
25. (16) N-Oxide was formed in 94% yield upon treatment of 4-bromo-7-azaindole 6 with a solution of 32% peracetic acid/acetic acid in ethyl acetate.
26. (a) Differding, E.; Ofner, H. Synlett 1991, 187.
27. (b) Barnes, K. D.; Hu, Y.; Hunt, D. A. Synth. Commun. 1994, 24, 1749.
28. (c) Zajc, B. J. Org. Chem. 1999, 64, 1902.
29. (a) Griffen, E. J.; Roe, D. G.; Snieckus, V. J. Org. Chem. 1995, 60, 1484.
30. (b) Beswick, P. J.; Greenwood, C. S.; Mowlem, T. J.; Nechvatal, G.; Widdowson, D. A. Tetrahedron 1988, 44, 7325.
31. (c) Sundberg, R. J.; Russell, H. F. J. Org. Chem. 1973, 41, 3324.
32. (d) Iwao, M. Heterocycles 1993, 36, 29.
33. (e) Bray, B. L.; Mathies, P. H.; Naef, R.; Solas, D. R.; Tidwell, T. T.; Artis, D. R.; Muchowski, J. M. J. Org. Chem. 1990, 55, 6317.
34. (19) A > 1.5 M solution of tert-butyllithium in pentane was used to avoid the precipitation of N-fluorobenzenesulfimide.