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 scale in
76% yield.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.