Highly effective synthesis of primary sulfonamides

ORGN 160

Alexander A Greenfield, greenfa@wyeth.com and Cristina Grosanu, grosanc@wyeth.com. Chemical and Screening Sciences, Wyeth Research, CN 8000, Princeton, NJ 08543
Primary sulfonamides represent a useful structural motif in biologically active molecules. Their syntheses, though conceptually simple and straightforward, often suffer from low to moderate yields. In our search for a universal high yielding synthetic method amenable for parallel syntheses we found two major obstacles: 1/ formation of bis- sulfonylated materials and/or 2 / insufficient conversion. Herein we describe an efficient protocol for a one pot synthesis of primary sulfonamides featuring utilization of excess of sulfonylating agent followed by base mediated recovery of the primary sulfonamide. The scope of the process and its applicability will be discussed