Expedient Synthesis of 4(5)-[1-(2,3-Dimethylphenyl)ethyl]-1<i>H</i>-imidazole, the α₂-Adrenergic Agonist Medetomidine

Abstract

(±)-4(5)-[1-(2,3-Dimethylphenyl)ethyl]-1H-imidazole hydrochloride (5) is prepared in three steps in 79% overall yield from 1-(N,N-dimethylsulfamoyl) imidazole by bis-protection, regioselective lithiation followed by an efficient tandem addition-reduction of the resulting 2,3-dimethylbenzoyl chloride adduct with lithium/ammonia/ammonium chloride.