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

被引：74

作者：

Cai, DW

Hughes, DL

Verhoeven, TR

机构：

[1] Department of Process Research, Merck Research Laboratories, Rahway, NJ 07065

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 15期

关键词：

D O I：

10.1016/0040-4039(96)00336-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Mono-lithiation of 2,6-dibromopyridine by n-BuLi is complicated by deprotonation 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-halogen exchange between 2,6-dibromopyridine and 2,6-dilithiopyridine produces 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

引用

页码：2537 / 2540

页数：4

共 14 条

[1]

[Anonymous], COMMUNICATION

[2]

CRAM DJ, 1978, Patent No. 4080337

[3]

DIVEKAR PV, 1972, CAN J CHEM, V45, P1215

[4] PYRIDYLLITHIUM COMPOUNDS [J].