A STUDY OF THE LITHIATION OF 2,6-DIBROMOPYRIDINE WITH BUTYLLITHIUM, AND ITS APPLICATION TO SYNTHESIS OF L-739,010

Authors
CAI DW HUGHES DL VERHOEVEN TR
Citation
Dw. Cai et al., A STUDY OF THE LITHIATION OF 2,6-DIBROMOPYRIDINE WITH BUTYLLITHIUM, AND ITS APPLICATION TO SYNTHESIS OF L-739,010, Tetrahedron letters, 37(15), 1996, pp. 2537-2540
Citations number
14
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
15
Year of publication
1996
Pages
2537 - 2540
Database
ISI
SICI code
0040-4039(1996)37:15<2537:ASOTLO>2.0.ZU;2-O
Abstract
Mono-lithiation of 2,6-dibromopyridine by n-BuLi is complicated by dep rotonation of the pyridine ring by the resulting mono-lithium species. This problem can be eliminated by a reverse addition, but this causes formation of the undesired dilithio species. However, rapid lithium-h alogen exchange between 2,6-dibromopyridine and 2,6-dilithiopyridine p roduces 2-brom-6-lithiopyridine cleanly. Thus, using reverse addition, the mono-lithiated pyridine can be generated in 98% yield. Copyright (C) 1996 Elsevier Science Ltd