title: Mild Pd-catalyzed N-arylation of methanesulfonamide and related nucleophiles: avoiding potentially genotoxic reagents and byproducts.
abstract: A convenient, general, and high yielding Pd-catalyzed cross-coupling of methanesulfonamide with aryl bromides and chlorides is reported. The use of this method 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.
authors.affiliation: Eli Lilly and Company, Lilly Corporate Center, Indianapolis, Indiana 46285, United States.
authors.forename: Brandon R
authors.initials: BR
authors.lastname: Rosen
authors.forename: J Craig
authors.initials: JC
authors.lastname: Ruble
authors.forename: Thomas J
authors.initials: TJ
authors.lastname: Beauchamp
authors.forename: Antonio
authors.initials: A
authors.lastname: Navarro
mesh_terms: D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D006842:Hydrocarbons, Brominated / Q000737:chemistry; D006843:Hydrocarbons, Chlorinated / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D010627:Phenethylamines / Q000138:chemical synthesis* / Q000737:chemistry; D013449:Sulfonamides / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D006842:Hydrocarbons, Brominated; D006843:Hydrocarbons, Chlorinated; D010627:Phenethylamines; D013449:Sulfonamides; C036871:methanesulfonamide; D010165:Palladium; C063533:dofetilide