Regioselective Synthesis of 1-Aklyl-4-(3-pyridyl)-Substituted Imidazole

A practical and regioselective synthesis of 1-alkyl-4-(3-pyridyl) imidazole via a Suzuki coupling reaction employing 3-pyridylboronates has been investigated. The use of sec-butyllithium in place of n-butyllithium for complete selectivity in removing bromines on tribromoimidazole to provide a key bromoimidazole coupling unit is described. For effective Suzuki coupling reaction, the nature of pyridylboronates and the conditions employed are discussed. The factors affecting the outcome of the Suzuki coupling reaction are presented.