A novel and efficient synthesis of 11H-indeno[1',2':4,5]imidazo[1,2-a]pyridin-11-one, a hybrid structure of indenone with imidazo[1,2-a]pyridine, from the reaction of 2-(2-bromophenyl)imidazo[1,2-a]pyridine with carbon monoxide through palladium-catalyzed CO insertion and C-H bond activation, has been developed. Intriguingly, under similar conditions but in the presence of Cu(OAc)2, the reaction selectively afforded 6H-chromeno[4',3':4,5]imidazo[1,2-a]pyridin-6-one, a hybrid structure of chromenone with imidazo[1,2-a]pyridine, via a more sophisticated cascade process including acetoxylation, deacetylation, CO insertion, and C-H bond activation.