Synthetic process development and scale up of palladium-catalyzed alkoxycarbonylation of chloropyridines

2,3-Dichloropyridines undergo a mono- or a dicarbonylation in the presence of carbon monoxide, an alcohol, and a palladium catalyst, affording selectively either alkyl 3-chloropyridine-2-carboxylates or dialkyl pyridine-2,3-dicarboxylates in good yields, depending on the reaction conditions. For instance, the process could be scaled up for the monoalkoxycarbonylation of 2,3-dichloro-5-(trifluoromethyl)pyridine, affording in high yield and selectivity the corresponding 3-chloro-5-(trifluoromethyl)pyridine-2-carboxylate.