Abstract Halogenation of 2-unsubstituted and 2-methylimidazo [4, 5-b] pyridines and their N- methyl derivatives with bromine and chlorine in acetic acid takes different pathways, depending on the acetic acid concentration. The bromination in 50% aqueous acetic acid gives only 6-bromoimidazo [4, 5-b] pyridines; bromination and chlorination of 2- unsubstituted imidazo [4, 5-b] pyridines in glacial acetic acid leads to 5, 6-dibromo ( ...