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Mild Pd-Catalyzed N-Arylation of Methanesulfonamide and Related Nucleophiles: Avoiding Potentially Genotoxic Reagents and Byproducts

Brandon R. Rosen, J. Craig Ruble*, Thomas J. Beauchamp and Antonio Navarro

*Eli Lilly and Company, Lilly Corporate Center, Indianapolis, Indiana 46285, United States, Email: ruble_craiglilly.com

B. R. Rosen, J. C. Ruble, T. J. Beauchamp, A. Navarro, Org. Lett., 2011, 13, 2564-2567.

DOI: 10.1021/ol200660s


Abstract

A convenient, general, and high yielding Pd-catalyzed cross-coupling of methanesulfonamide with aryl bromides and chlorides eliminates concern over genotoxic impurities that can arise when an aniline is reacted with methanesulfonyl chloride. The application of this method to the synthesis of dofetilide is also reported.


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Key Words

Sulfonamides


ID: J54-Y2011-1440