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Preparation of Substituted Benzimidazoles and Imidazopyridines Using 2,2,2-Trichloroethyl Imidates

Stéphane Caron*, Brian P. Jones, Lulin Wei

*Chemical R&D, Pfizer Worldwide R&D, MS-8118D/4002, Eastern Point Rd, Groton CT 06340, USA, Email: stephane.caronpfizer.com

S. Caron, B. P. Jones, L. Wei, Synthesis, 2012, 44, 3049-3054.

DOI: 10.1055/s-0032-1317019


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Abstract

The preparation of benzimidazoles and imidazopyridines proceeds smoothly under mild conditions in isopropyl alcohol at 70°C using 2,2,2-trichloroethyl imidates as the acylating agents. Addition of sodium acetate proved to be beneficial In cases where cyclization proceeded slowly. For substrates with poor nucleophilicity, using the more inert tert-amyl alcohol enabled superior reactions.

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Key Words

benzimidazoles, imidazopyridines, imidates, 1,2-diaminoarenes, cyclization


ID: J66-Y2012-3250