Synthesis of Disubstituted 3-Phenylimidazo[1,2-a]pyridines via a 2-Aminopyridine/CBrCl₃ α-Bromination Shuttle

Irwan Iskandar Roslan, Kian-Hong Ng, Ji'-En Wu, Gaik-Khuan Chuah* and Stephan Jaenicke*

*Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore, Singapore 117543, Email: chmsjnus.edu.sg, chmcgknus.edu.sg

I. I. Roslan, K.-H. Ng, J.-E. Wu, G.-K. Chuah, S. Jaenicke, J. Org. Chem., 2016, 81, 9167-9174.

DOI: 10.1021/acs.joc.6b01714

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Abstract

A coupling of 2-aminopyridine with phenylacetophenones, phenylacetones, or β-tetralone in the presence of CBrCl₃ provides disubstituted 3-phenylimidazo[1,2-a]pyridine in very good isolated yields at 80°C within 5 h. The 2-aminopyridine acts as an α-bromination shuttle by transferring Br from CBrCl₃ to the α-carbon of the carbonyl moiety.

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Key Words

imidazo[1,2-a]pyridines

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ID: J42-Y2016