Synthesis of 4-alkyl-3,5-dibromo-, 3-bromo-4,5-dialkyl-and 3,4,5-trialkylpyridines via sequential metalation and metal-halogen exchange of 3,5-dibromopyridine

Tetrahedron Letters

Volumn 37, Issue 15, 1996, Pages 2565-2568

  Gu, Yu Gui ^a   Bayburt, Erol K ^a  

^a ABBOTT LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOBROMINE DERIVATIVE; PYRIDINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029868536     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00331-0     Document Type: Article

References (16)

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3. For reviews, see: a) Rewcastle, G. W.; Katritzky, A. R. Adv. Heterocycl. Chem. 1993, 56, 155.
4. b) Queguiner, G.; Marsais, F.; Snieckus, V.; Epsztajn, J. Adv. Heterocycl. Chem. 1991, 52, 187.
5. Gribble, G.W.; Saulnier, M. G. Tetrahedron Lett. 1980, 21, 4137.
6. Rocca, P.; Cochennec, C.; Massais, F.; Thomas-dit-Dumont, L.; Mallet, M.; Godard, A.; Queguiner, G. J. Org. Chem. 1993, 58, 7832 and references cited therein.
7. a) Mallet, M.; Queguiner, G. Tetrahedron 1979, 35, 1625.
8. b) Mallet, M.; Queguiner, G. Tetrahedron 1982, 38, 3035.
9. c) Mallet, M.; Queguiner, G. Tetrahedron 1986, 42, 2253.
10. 3) and mass spectra.
11. Cale, A. D. Jr.; Gero, T. W.; Walker, K. R.; Lo, Y. S.; Welstead, W. J. Jr.; Jaques, L. W.; Johnson, A. F.; Leonard, C. A.; Nolan, J. C.; Johnson, D. N. J. Med. Chem. 1989, 32(9), 2178.
12. Marsais, F.; Breant, P.; Ginguene, A.; Queguiner, G. J. Organomet. Chem. 1981, 216, 139.
13. Kauffmann, T.; Angew. Chem., Int. Ed. Engl. 1919,18,1.
14. Mallet, M.; Queguiner, G. Tetrahedron 1985 421, 3433.
15. 4Cl, whereas 3b was isolated as a sole product in 82% yield when the same reaction was conducted in THF at -78°C for less than 2h.
16. 3) δ 8.65 (s, 1H), 8.63 (s, 1H), 7.40-7.28 (m, 5H), 6.07 (s, 1H), 5.87-5.72 (m, 1H), 5.09 (d, J=10.5 Hz, 1H), 4.91 (d, J=16.5 Hz, 1H), 3.68-3.42 (m, 2H), 2.40 (s br, 1H).