A study of the lithiation of 2,6-dibromopyridine with butyllithium, and its application to synthesis of L-739,010

Tetrahedron Letters

Volumn 37, Issue 15, 1996, Pages 2537-2540

  Cai, Dongwei ^a   Hughes, David L ^a   Verhoeven, Thomas R ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3 [6 [7 CYANO 5 (3 FURYL) 2 NAPHTHOXYMETHYL] 2 PYRIDYL] 3 HYDROXY 6,8 DIOXABICYCLO[3.2.1]OCTANE; LIPOXYGENASE INHIBITOR;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0029980473     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00336-X     Document Type: Article

References (15)

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4. (a) Lehn, J.-M. Angew. Chem. Int. Ed. Eng. 1988, 27, 89; 1990, 29, 1304;
5. (a) Lehn, J.-M. Angew. Chem. Int. Ed. Eng. 1988, 27, 89; 1990, 29, 1304;
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7. Queguiner, G,; Marsais, F.; Snieckus, V.; Epsztajn, J. "Advances of Heterocyclic Chemistry" V52, p189-304, Academic Press, San Diego, CA 1991.
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11. (a) Parks, J. E.; Wagner, B. E.; Holm, R. H. J. Organomet. Chem. 1973, 56, 53.
12. (b) Utimoto, K.; Sakai, N.; Nozaki, H. J. Am. Chem. Soc. 1974, 96, 5601.
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14. (d) Tsukube, H.; Uenishi, J.; Higaki, H.; Kikkawa, K.; Tanaka, T.; Wakabayashi, S.; Oae, S. J. Org. Chem. 1993, 58, 4389
15. 4, and concentrated to obtain the desired product, 2-bromo-6-hydroxymethyl-pyridine, as a pale yellow oil (9.25g, 98%), which has 98 wt% purity as assayed by HPLC.