A new solvent/ligand controlled switchable C–H arylation of 1-methyl-4-nitro-1H-indazole catalyzed by Pd(OAc)2 was achieved. A bidentate ligand in DMA promoted the activation at C7 position, while a phosphine ligand in H2O oriented the arylation at C3 position. The C3 and C7 arylation products were obtained in moderate to good yields and in high regioselectivity.

A regioselective C7-bromination of 4-substituted 1H-indazoles followed by a palladium-catalyzed Suzuki–Miyaura reaction with boronic acids is described.