Scalable and Straightforward Synthesis of a 2-Alkyl-7-Arylbenzo­thiophene as a GPR52 Agonist via a Hemithioindigo Derivative

Abstract A simple and efficient procedure has been developed for the synthesis of the GPR52 agonist N -(2-amino-2-oxoethyl)-3-{4-fluoro-2-[3-(trifluoromethyl)benzyl]-1-benzothien-7-yl}benzamide. The benzo­thiophene unit was directly constructed by reduction of a hemithioindigo derivative prepared by...

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Bibliographic Details
Published in:Synthesis (Stuttgart) 2015-08, Vol.47 (22), p.3467-3472
Main Authors: Fukuda, Naohiro, Ikemoto, Tomomi
Format: Article
Language:English
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Summary:Abstract A simple and efficient procedure has been developed for the synthesis of the GPR52 agonist N -(2-amino-2-oxoethyl)-3-{4-fluoro-2-[3-(trifluoromethyl)benzyl]-1-benzothien-7-yl}benzamide. The benzo­thiophene unit was directly constructed by reduction of a hemithioindigo derivative prepared by an intramolecular Friedel–Crafts cyclization of (phenylsulfanyl)acetic acid, followed by dehydrative benzylidene formation.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0034-1378746