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Synlett 1990; 1990(4): 207-208
DOI: 10.1055/s-1990-21035
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Synthesis of Protected Indoles from N-(tert-Butoxycarbonyl)-2-alkylanilines

Robin D. Clark* , Joseph M. Muchowski, Michel Souchet, David B. Repke
  • *Syntex Research, Institute of Organic Chemistry, 3401 Hillview Ave., Palo Alto, California 94304, USA
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Publication Date:
08 March 2002 (online)

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Dilithiation of N-(tert-butoxycarbonyl)-2-alkylanilines with sec-butyllithium followed by addition of dimethylformamide and treatment with hydrochloric acid affords tert-butoxycarbonyl-protected indoles. Reaction of the dilithio species with N-methoxy-N-methylamides followed by treatment with trifluoroacetic acid affords 2-substituted indoles.