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

Autor: Ming Tao, Reddeppareddy Dandu, Kurt A. Josef, Robert L. Hudkins, Edward R. Bacon
Rok vydání: 2007
Předmět:
Zdroj: Journal of Heterocyclic Chemistry. 44:437-440
ISSN: 1943-5193
0022-152X
DOI: 10.1002/jhet.5570440225
Popis: A regiospecific approach to each N-methyl-5-(1H-indol-2-yl)-6,7-dihydro-2H-indazole isomer is reported. The 1-methyl isomer 1 was prepared from 5-bromo-1-methyl-6,7-dihydro-1H-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-1H-indole-2-yl)lithium 6 with 2-methyl-2,4,6,7-tetrahydro-indazol-5-one 8 followed by acid catalyzed dehydration.
Databáze: OpenAIRE