Development of a pilot-plant process for a nevirapine analogue HIV NNRT inhibitor

…, M Sarvestani, R Simpson, R Varsolona…

Index: Busacca, Carl A.; Cerreta, Mike; Dong, Yong; Eriksson, Magnus C.; Farina, Vittorio; Feng, XuWu; Kim, Ji-Young; Lorenz, Jon C.; Sarvestani, Max; Simpson, Robert; Varsolona, Rieh; Vitous, Jana; Campbell, Scot J.; Davis, Mark S.; Jones, Paul-James; Norwood, Daniel; Qiu, Fenghe; Beaulieu, Pierre L.; Duceppe, Jean-Simon; Hache, Bruno; Brong, Jim; Chiu, Fang-Ting; Curtis, Tom; Kelley, Jason; Lo, Young S.; Powner, Tory H. Organic Process Research and Development, 2008 , vol. 12, # 4 p. 603 - 613

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Citation Number: 17

Abstract

The pilot-plant synthesis of nevirapine analogue 1 is described. The compound was prepared in eight steps from substituted pyridine raw materials and 4-hydroxyquinoline. The key transformation involves a novel one-pot conversion of an arylhalide to arylacetic acid under palladium catalysis, followed by regioselective reduction via in situ generated BH3/THF to the arylethanol intermediate 2. All stages were carried out on 10− 150-kg ...