Versatile synthesis of 3,5-disubstituted 2-fluoropyridines and 2-pyridones

Journal of Organic Chemistry

Volumn 68, Issue 8, 2003, Pages 3352-3355

  Sutherland, Andrew ^a   Gallagher, Timothy ^a  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

SUZUKI REACTION;

BROMINE COMPOUNDS; ORGANIC ACIDS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

FLUORINE COMPOUNDS;

2 BROMO 2 FLUORO 3 PYRIDYLBORONIC ACID DERIVATIVE; 2 FLUOROPYRIDINE DERIVATIVE; 2 PYRIDONE DERIVATIVE; 5 BROMO 2 FLUOROPYRIDINE DERIVATIVE; BORONIC ACID DERIVATIVE; IODIDE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; LITHIATION; REACTION ANALYSIS; STRUCTURE ANALYSIS; SUZUKI REACTION; SYNTHESIS;

EID: 0037453681     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026864f     Document Type: Article

References (29)

1. (a) Gribble, G. W.; Saulnier, M. G. Heterocycles 1993, 35, 151-169.
2. (b) Gribble, G. W.; Saulnier, M. G. Tetrahedron Lett. 1980, 21, 4137-4140.
3. (a) Güngör, T.; Marsais, F.; Quéguiner, G. J. Organomet. Chem. 1981, 215, 139-150.
4. (b) Marsais, F.; Laperdrix, B.; Güngör, T.; Mallet, M.; Quéguiner, G. J. Chem. Res., Synop. 1982, 278-279.
5. (c) Mallet, M.; Quéguiner, G. Tetrahedron 1985, 41, 3433-3440.
6. (d) Mallet, M.; Quéguiner, G. Tetrahedron 1982, 38, 3035-3042.
7. (e) Mallet, M.; Quéguiner, G. Tetrahedron 1986, 42, 2253-2262.
8. (f) Mallet, M.; Branger, G.; Marsais, F.; Quéguiner, G. J. Organomet. Chem. 1990, 382, 319-332.
9. (g) Marsais, F.; Pineau, P.; Nivolliers, F.; Mallet, M.; Turck, A.; Godard, A.; Quéguiner, G. J. Org. Chem. 1992, 57, 565-573.
10. (h) Rocca, P.; Cochennec, C.; Marsais, F.; Thomas-dit-Dumont, L.; Mallet, M.; Godard, A.; Quéguiner, G. J. Org. Chem. 1993, 58, 7832-7838.
11. For reviews, see: Quéguiner, G.; Marsais, F.; Snieckus, V.; Epsztajn, J. Adv. Heterocycl. Chem. 1991, 52, 187-304.
12. Mongin, F.; Quéguiner, G. Tetrahedron 2001, 57, 4059-4090.
13. (a) Karig, G.; Spencer, J. A.; Gallagher, T. Org. Lett. 2001, 3, 835-838.
14. (b) Karig, G.; Thasana, N.; Gallagher, T. Synlett 2002, 808-810.
15. (a) Bouillon, A.; Lancelot, J. C.; Collot, V.; Bovy, P. R.; Rault, S. Tetrahedron 2002, 58, 4369-4373.
16. (b) Bouillon, A.; Lancelot, J. C.; Collot, V.; Bovy, P. R.; Rault, S. Tetrahedron 2002, 58, 3323-3328.
17. (c) Bouillon, A.; Lancelot, J. C.; Collot, V.; Bovy, P. R.; Rault, S. Tetrahedron 2002, 58, 2885-2890.
18. Parry, P. R.; Wang, C.; Batsanov, A. S.; Bryce, M. R.; Tarbit, B. J. Org. Chem. 2002, 67, 7541-7543.
19. Tagat, J. R.; McCombie, S. W.; Barton, B. E.; Jackson, J.; Shortall, J. Bioorg. Med. Chem. Lett. 1995, 5, 2143-2146.
20. Negishi, E.; Luo, F. T.; Frisbee, R.; Matsushita, H. Heterocycles 1982, 18, 117-122.
21. Unsuccessful Li-Zn exchange of the 3-lithiated species of 5-bromo-2-fluoropyridine 7 was expected, as similar results with the corresponding lithiated species of 2-fluoropyridine during the synthesis of fluoro analogues of UB-165 were observed. For a discussion of these results, see: Sutherland, A.; Gallagher, T.; Sharples, C. G. V.; Wonnacott, S. J. Org. Chem. 2003, 68, 2475-2478.
22. For the synthesis of other dihalopyridyl boronic acids, see: Achad, S.; Guyot, M. Potier, P. Tetrahedron Lett. 1993, 34, 2127-2130. Mongin, F.; Trécourt, F.; Gervais, B.; Mongin, O.; Quéguiner G. J. Org. Chem. 2002, 67, 3272-3276. 2,6-Difluoropyridyl 3- and 4-boronic acids have been reported in the patent literature: Reiffenrath, V. Ger. Offen. 4218978, 1993. Boyd, F. L.; Gudmundsson, K.; Johns, B. A. WO 0278701, 2002. Alberti, M. J.; Baldwin, I. R.; Cheung, M.; Cockerill, S.; Flack, S.; Harris, P. A.; Jung, D. K.; Peckham, G.; Peel, M. R.; Stanford, J. B.; Stevens, K.; Veal, J. M. WO 0216359, 2002.
23. For the synthesis of other dihalopyridyl boronic acids, see: Achad, S.; Guyot, M. Potier, P. Tetrahedron Lett. 1993, 34, 2127-2130. Mongin, F.; Trécourt, F.; Gervais, B.; Mongin, O.; Quéguiner G. J. Org. Chem. 2002, 67, 3272-3276. 2,6-Difluoropyridyl 3- and 4-boronic acids have been reported in the patent literature: Reiffenrath, V. Ger. Offen. 4218978, 1993. Boyd, F. L.; Gudmundsson, K.; Johns, B. A. WO 0278701, 2002. Alberti, M. J.; Baldwin, I. R.; Cheung, M.; Cockerill, S.; Flack, S.; Harris, P. A.; Jung, D. K.; Peckham, G.; Peel, M. R.; Stanford, J. B.; Stevens, K.; Veal, J. M. WO 0216359, 2002.
24. For the synthesis of other dihalopyridyl boronic acids, see: Achad, S.; Guyot, M. Potier, P. Tetrahedron Lett. 1993, 34, 2127-2130. Mongin, F.; Trécourt, F.; Gervais, B.; Mongin, O.; Quéguiner G. J. Org. Chem. 2002, 67, 3272-3276. 2,6-Difluoropyridyl 3- and 4-boronic acids have been reported in the patent literature: Reiffenrath, V. Ger. Offen. 4218978, 1993. Boyd, F. L.; Gudmundsson, K.; Johns, B. A. WO 0278701, 2002. Alberti, M. J.; Baldwin, I. R.; Cheung, M.; Cockerill, S.; Flack, S.; Harris, P. A.; Jung, D. K.; Peckham, G.; Peel, M. R.; Stanford, J. B.; Stevens, K.; Veal, J. M. WO 0216359, 2002.
25. For the synthesis of other dihalopyridyl boronic acids, see: Achad, S.; Guyot, M. Potier, P. Tetrahedron Lett. 1993, 34, 2127-2130. Mongin, F.; Trécourt, F.; Gervais, B.; Mongin, O.; Quéguiner G. J. Org. Chem. 2002, 67, 3272-3276. 2,6-Difluoropyridyl 3- and 4-boronic acids have been reported in the patent literature: Reiffenrath, V. Ger. Offen. 4218978, 1993. Boyd, F. L.; Gudmundsson, K.; Johns, B. A. WO 0278701, 2002. Alberti, M. J.; Baldwin, I. R.; Cheung, M.; Cockerill, S.; Flack, S.; Harris, P. A.; Jung, D. K.; Peckham, G.; Peel, M. R.; Stanford, J. B.; Stevens, K.; Veal, J. M. WO 0216359, 2002.
26. For the synthesis of other dihalopyridyl boronic acids, see: Achad, S.; Guyot, M. Potier, P. Tetrahedron Lett. 1993, 34, 2127-2130. Mongin, F.; Trécourt, F.; Gervais, B.; Mongin, O.; Quéguiner G. J. Org. Chem. 2002, 67, 3272-3276. 2,6-Difluoropyridyl 3- and 4-boronic acids have been reported in the patent literature: Reiffenrath, V. Ger. Offen. 4218978, 1993. Boyd, F. L.; Gudmundsson, K.; Johns, B. A. WO 0278701, 2002. Alberti, M. J.; Baldwin, I. R.; Cheung, M.; Cockerill, S.; Flack, S.; Harris, P. A.; Jung, D. K.; Peckham, G.; Peel, M. R.; Stanford, J. B.; Stevens, K.; Veal, J. M. WO 0216359, 2002.
27. 6 examined the Suzuki reaction of a bromopyridyl boronic acid, and under extended reaction times (22-43 h) in DMF, only low yields (10-32%) of the coupled products were isolated.
28. Solomon, M. S.; Hopkins, P. B. Tetrahedron Lett. 1991, 32, 3297-3300.
29. Bradlow, L.; Vanderwerf, C. A. J. Org. Chem. 1949, 14, 509-515.