A scalable method for the preparation of oxindole 8, a key intermediate en route to a serine palmitoyl transferase inhibitor, compound 1, is presented. A three-step, chromatography-free route has been designed that takes advantage of Buchwald's palladium-catalyzed C–H functionalization to cyclize an α-chloroacetanilide to form the five-membered ring. This process has been successfully carried out in our kilogram laboratory facility on 10-kg ...
