Kilogram-Lab-Scale Oxindole Synthesis via Palladium-Catalyzed C–H Functionalization

EJ Kiser, J Magano, RJ Shine…

Index: Kiser, E. Jason; Magano, Javier; Shine, Russell J.; Chen, Michael H. Organic Process Research and Development, 2012 , vol. 16, # 2 p. 255 - 259

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Citation Number: 14

Abstract

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 ...