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Paper | Regular issue | Vol 32, No. 4, 1991, pp.685-692
Published online, 1st January, 1970
DOI: 10.3987/COM-90-5446
Regio- and Chemoselective Alkylation of 2,3-Dialkylindoles. A Convenient Preparation of 2,3,3-Trialkyl-3H-indoles

Colin W. G. Fishwick,* Andrew D. Jones, and Michael B. Mitchell

*School of Chemistry, The University of Leeds, Leeds, LS2 9JT, U.K.

Abstract

Various 3-alkyl-2,3-dimethyl-3H-indoles were prepared by addition of an alkyl iodide to a solution of the lithium salt of 2,3-dimethylindole. In contrast, reaction with ethyl chloroformate or trimethylsilyl chloride afforded the N-substituted indoles exclusively. The reaction failed with cyclohexylcarboxaldehyde.