There is significant interest in the development of process routes for active pharmaceutical ingredients using C−H arylation methodology. An efficient and practical synthetic route for Febuxostat (<b>1</b>), which was developed by Teijin Pharma Ltd. and approved as the first non-purine-type inhibitor of xanthine oxidase since allopurinol, has been established via palladium- and copper-catalyzed C−H arylation of thiazole with aryl bromide. The palladium-catalyst loading was reduced as low as 0.1 mol % for the intermolecular C−H arylation, and a three-step synthesis produced febuxostat in 89% overall yield with excellent selectivity.

Process development of febuxostat using palladium- and copper-catalyzed C−H arylation

2019 Spring National Meeting

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