A robust process for an mGluR5 negative allosteric modulator: Difluoromethylation and Sonogashira coupling on large scale

JB Sperry, RM Farr, M Levent, M Ghosh…

Index: Sperry, Jeffrey B.; Farr, Roger M.; Levent, Mahmut; Ghosh, Mousumi; Hoagland, Steven M.; Varsolona, Richard J.; Sutherland, Karen Organic Process Research and Development, 2012 , vol. 16, # 11 p. 1854 - 1860

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Citation Number: 10

Abstract

The development of the potent and selective mGluR5 negative allosteric modulator (NAM) 1 is described. Key features in the process, which has been implemented on a multikilogram scale, include a high-temperature difluoromethylation reaction, a Sonogashira coupling, and careful control of residual Pd and Cu in the final API. Due to the relative nonpolar nature of the intermediates, water-miscible solvents were employed in all four steps to allow for ...

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