An Efficient Synthesis of 2-Ethyl-7-chloro-4-methylthieno[4,3,2-e,f][3]benzazepine (SK&F 106686) via Bromomethylation of 2-Ethyl-5-chlorobenzo[b]thiophene

L. N. Pridgen Synthetic Chemistry Department, SmithKline Beecham Pharmaceuticals, Post Office Box 1539, King of Prussia, PA, 19406-0939

K. Huang Synthetic Chemistry Department, SmithKline Beecham Pharmaceuticals, Post Office Box 1539, King of Prussia, PA, 19406-0939

R. J. Mills Synthetic Chemistry Department, SmithKline Beecham Pharmaceuticals, Post Office Box 1539, King of Prussia, PA, 19406-0939

S. Shilcrat Synthetic Chemistry Department, SmithKline Beecham Pharmaceuticals, Post Office Box 1539, King of Prussia, PA, 19406-0939

A. Tickner Synthetic Chemistry Department, SmithKline Beecham Pharmaceuticals, Post Office Box 1539, King of Prussia, PA, 19406-0939

Abstract

The synthesis of 2-ethyl-3-bromoethyl-5-chlorobenzo[b]thiophene (6) is described using a unique phase transfer catalyzed bromoethylation of 2-ethyl-5-chlorobenzo[b]thiophene (5). Compound 6 was converted in six steps and in 55% overall yield to the angiotension II antagonist, SK&F 106686 (1).

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An Efficient Synthesis of 2-Ethyl-7-chloro-4-methylthieno[4,3,2-e,f][3]benzazepine (SK&F 106686) via Bromomethylation of 2-Ethyl-5-chlorobenzo[b]thiophene

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An Efficient Synthesis of 2-Ethyl-7-chloro-4-methylthieno[4,3,2-e,f][3]benzazepine (SK&F 106686) via Bromomethylation of 2-Ethyl-5-chlorobenzo[b]thiophene

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