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C-2 side chain alkylation of 2-methyl-3-alkylindoles via 3-methoxyindolenines:
Authors:Susan F Vice  Edward A Gross  Richard W Friesen  Gary I Dmitrienko
Institution:The Guelph-Waterloo Centre for Graduate Work in Chemistry, Waterloo Campus, Department of Chemistry, University of Waterloo, Waterloo, Ontario, Canada N2L 3G1
Abstract:3-Methoxyindolenines derived from 2-methyl-3-alkylindoles by bromination-methanolysis undergo base induced alkylations and aldol condensations at the C-2 methyl group. The modified indolenines can be efficiently converted to C-2-sides chain alkylated indoles by reduction with lithium-aluminum hydride or zinc.
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