One-Pot and Regiospecific Synthesis of 2,3-Disubstituted Indoles from 2-Bromoanilides via Consecutive Palladium-Catalyzed Sonogashira Coupling, Amidopalladation, and Reductive Elimination

Bruce Z. Lu*, Han-Xun Wei, Yongda Zhang, Wenyi Zhao, Marine Dufour, Guisheng Li, Vittorio Farina and Chris H. Senanayake

*Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, Ridgefield, Connecticut 06877, United States, Email: bruce.luboehringer-ingelheim.com

B. Z. Lu, H.-X. Wei, Y. Zhang, W. Zhao, M. Dufour, G. Li, V. Farina, C. H. Senanayake, J. Org. Chem., 2013, 78, 4558-4562.

DOI: 10.1021/jo302679f

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Abstract

A practical one-pot and regiospecific three-component process gives 2,3-disubstituted indoles from 2-bromoanilides via consecutive palladium-catalyzed Sonogashira coupling, amidopalladation, and reductive elimination.

see article for more examples

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A Practical Mild, One-Pot, Regiospecific Synthesis of 2,3-Disubstituted Indoles via Consecutive Sonogashira and Cacchi Reactions

B. Z. Lu, W. Zhao, H.-X. Wei, M. Dufour, V. Farina, C. H. Senanayake, Org. Lett., 2006, 8, 3271-3274.

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Key Words

Indoles, Multicomponent Reactions, Sonogashira Coupling

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ID: J42-Y2013