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ACS Comb Sci. 2011 Mar 14;13(2):140-6. doi: 10.1021/co100040z. Epub 2010 Dec 17.

One-pot synthesis of 2-amino-indole-3-carboxamide and analogous.

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  • 1Drug Discovery Institute, University of Pittsburgh, Pittsburgh, PA 15261, United States.

Abstract

An efficient one-pot, two-step solution-phase synthetic method was developed to synthesize twenty-three 2-amino-indole-3-carboxamides (3) from 2-halonitrobenzene (1) or heterocyclic analogous and cyanoacetamides (2). In this sequence, first, intermediate 2-cyano-2-(2-nitrophenyl)acetamide (4) was generated under basic condition via S(NAr) reaction; after direct addition of hydrochloric acid solution, FeCl(3), and Zn powder, indole 3 was generated via reduction/cyclization process.

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