Synthesis of 2-methyl-4-methoxydiphenylamine by palladium catalyzed C–N coupling—high synthetic versatility by use of a flexible catalytic system

The synthetic versatility of the Buchwald–Hartwig Amination is demonstrated by the synthesis of the industrially important intermediate 2-methyl-4-methoxydiphenylamine. Using four routes differing in the choice of the starting materials, the diarylamine could be synthesized in excellent yields, however, each reaction required a different combination of ligand, base and solvent. This new approach is compared to established industrial routes.