N-Aryl sulfonamides are an important class of compound in both pharmaceutical and natural products. During the recent development of the synthesis of an active pharmaceutical ingredient, we employed a key palladium-catalyzed carbon-nitrogen bond formation step to assemble an aryl sulfonamide core. A detailed mechanistic study of this reaction was performed to examine the formation of the observed impurities and the step was demonstrated on 61 kg scale (84% yield).This presentation will describe both the development and mechanistic investigation of this process as well as a novel extension of the methodology to the convergent synthesis of phenoxazines.

Development and investigation of Pd-catalyzed C-N bond formation: Application to the synthesis of an active pharmaceutical ingredient

245th National Meeting (2013)

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