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

Stéphane Caron; Brian P. Jones; Lulin Wei

doi:10.1055/s-0032-1317019

Synthesis, Table of Contents

Synthesis 2012; 44(19): 3049-3054
DOI: 10.1055/s-0032-1317019

paper

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

Stéphane Caron*

Chemical R&D, Pfizer Worldwide R&D, MS-8118D/4002, Eastern Point Rd, Groton CT 06340, USA, Fax: +1(860)7158584 Email: stephane.caron@pfizer.com

,

Brian P. Jones

Chemical R&D, Pfizer Worldwide R&D, MS-8118D/4002, Eastern Point Rd, Groton CT 06340, USA, Fax: +1(860)7158584 Email: stephane.caron@pfizer.com

,

Lulin Wei

Chemical R&D, Pfizer Worldwide R&D, MS-8118D/4002, Eastern Point Rd, Groton CT 06340, USA, Fax: +1(860)7158584 Email: stephane.caron@pfizer.com

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Abstract

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Abstract

The preparation of benzimidazoles and imidazopyridines has been achieved under mild conditions using 2,2,2-trichloroethyl imidates as the acylating agents. The reactions proceed smoothly in isopropyl alcohol at 70 °C. In cases where the acylation was rapid but the cyclization proceeded slowly, addition of sodium acetate proved to be beneficial. For substrates with poor nucleophilicity, modification of the solvent to the more inert tert-amyl alcohol, which can also achieve higher temperature, allowed for superior reactions.

Key words

benzimidazole - imidazopyridine - imidate - 1,2-diaminoarene - cyclization

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References

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