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

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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Bibliographic Details
Published inSynthetic communications Vol. 28; no. 18; pp. 3479 - 3489
Main Authors Pridgen, L. N., Huang, K., Mills, R. J., Shilcrat, S., Tickner, A.
Format Journal Article
LanguageEnglish
Published NEW YORK Taylor & Francis Group 01.09.1998
Marcel Dekker Inc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ADRENOCEPTOR
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Summary: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).
ISSN:0039-7911
1532-2432
DOI:10.1080/00397919808004456