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Synlett 1997; 1997(11): 1312-1314
DOI: 10.1055/s-1997-1022
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Synthesis of 3-Alkoxyindoles via Palladium-Catalyzed Intramolecular Cyclization of N-Alkyl ortho-Siloxyallylanilines

Matthew Gowan, Alain S. Caillé, Cheuk K. Lau*
  • *Medicinal Chemistry Department, Merck Frosst Centre for Therapeutic Research, P.O. Box 1005, Pointe Claire-Dorval, Québec, H9R 4P8, Canada, Fax 1 514 695-0693; Internet lau@merck.com
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Publication Date:
31 December 2000 (online)

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Palladium-catalyzed intramolecular cyclization of N-alkyl-ortho-siloxyallylaniline leads to the synthesis of N-alkyl-3-siloxy-indoles. Treatment of the latter with fluoride followed by in situ trapping of the resulting alkoxides with various alkyl halides gives the corresponding N-alkyl-3-alkoxyindoles.

palladium - indoxyl - siloxyallylaniline - 3-alkoxyindol