Synthesis and Characterization of 2-Phenylimidazo[1,2-a]pyridine: A Privileged Structure for Medicinal Chemistry

A straightforward synthesis of 2-phenylimidazo[1,2-a]pyridine is described. The reaction is designed to demonstrate to students the preparation of a bridged N-heterocycle, in which the heteroatom occupies a bridgehead position. The product is obtained in moderate to high yield and is highly crystalline. The compound can be purified either by direct recrystallization or silica gel column chromatography. Students characterize the compound by melting point, MS, IR spectroscopy, and NMR spectroscopy. Spectroscopic analysis reveals features that are potentially suitable for more in-depth discussions.