[Abstract]Functionalization of 7-azaindole utilizing Reissert-Henze type reaction was studied. It was found that the direct halogenation, cyanation, and thiocyanation of 7-azaindole proceeded regioselectively. In chlorination of 7-azaindole, the regioselectivity was controlled by chlorination reagents as well as acylation reagents. These functional groups could be chemically modified to useful substituents