A scalable Nenitzescu synthesis of 2??methyl??4??(trifluoromethyl)??1H??indole??5??carbonitrile

EE Boros, I Kaldor, PS Turnbull

Index: Boros, Eric E.; Kaldor, Istvan; Turnbull, Philip S. Journal of Heterocyclic Chemistry, 2011 , vol. 48, # 3 p. 733 - 736

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Citation Number: 5

Abstract

Abstract 2-Methyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile is a key intermediate in the synthesis of selective androgen receptor modulators discovered in these laboratories. A practical and convergent synthesis of the title compound starting from 4-nitro-3- (trifluoromethyl) phenol and tert-butyl acetoacetate was developed, including a telescoped procedure for synthesis (without isolation) and Nenitzescu reaction of 2-trifluoromethyl-1, ...