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Regiospecific synthesis of 5-(1H-indol-2-yl)-1- and 2-methyl-6,7-dihydro-2H-indazole isomers

✍ Scribed by Reddeppareddy Dandu; Ming Tao; Kurt A. Josef; Edward R. Bacon; Robert L. Hudkins

Publisher: Journal of Heterocyclic Chemistry
Year: 2007
Tongue: English
Weight: 286 KB
Volume: 44
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570440225

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✦ Synopsis

Abstract

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A regiospecific approach to each N‐methyl‐5‐(1__H__‐indol‐2‐yl)‐6,7‐dihydro‐2__H__‐indazole isomer is reported. The 1‐methyl isomer 1 was prepared from 5‐bromo‐1‐methyl‐6,7‐dihydro‐1__H__‐indazole 3 and indole‐2‐boronate 5 by palladium catalyzed Suzuki coupling. The 2‐methyl regioisomer 2 was synthesized via addition of lithium (1‐carboxylato‐1__H__‐indole‐2‐yl)lithium 6 with 2‐methyl‐2,4,6,7‐tetrahydro‐indazol‐5‐one 8 followed by acid catalyzed dehydration.

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