Imidazo[1,2-a]pyridines were obtained by direct reaction of acetophenone, propiophenone, and their furan analogs and ring-substituted derivatives with an equimolar amount of iodine and and excess 2-aminopyridine or its substituted derivatives. The effect of substituents in the ketones and 2-aminopyridine, the reagent molar ratios, the character of the solvents, and replacement of iodine by other halogenating agents on the course of the reaction and the yields of products was studied. The formation of 3-iodo- and 6-iodoimidazopyridines as side products was noted in the case of ketones that do not have electron-acceptor substituents in the ring. These and other iodo-substituted imidazopyridines were synthesized for chromatographic comparison.