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

All articles of this category (±)-4(5)-[1-(2,3-Dimethylphenyl)ethyl]-1 H -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.