Selective lithiation of 2,3-dibromo-1-methylindole. A synthesis of 2,3-disubstituted indoles

被引：34
|
作者：
Liu, YB [1 ]
Gribble, GW [1 ]
机构：
[1] Dartmouth Coll, Dept Chem, Hanover, NH 03755 USA
来源：
TETRAHEDRON LETTERS | 2002年 / 43卷 / 40期
基金：
美国国家卫生研究院;
关键词：
2,3-dibromo-1-methylindole; 2,3-disubstituted indoles; lithiation; lithioindoles;
D O I：
10.1016/S0040-4039(02)01710-0
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Indole (1) can be converted to 2,3-dibromo-1-methylindole (3) in two operations (92% yield). Treatment of 3 with tert-butyllithium effects clean monolithiation to 3-bromo-2-lithio-1-methylindole (4), which can be trapped with various electrophiles to afford the 3-bromo-2-substituted indoles (5-8) in 85-99% yield. A second bromine-lithium exchange reaction and quenching with electrophiles yields the 2,3-disubstituted indoles (9-10) in 88-95% yield. (C) 2002 Published by Elsevier Science Ltd.
引用
收藏
页码：7135 / 7137
页数：3
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