Suppression of a palladium-mediated homocoupling in a Suzuki cross-coupling reaction. Development of an impurity control strategy supporting synthesis of …

…, AH Fray, JT Quatroche, CD Sturgill

Index: Miller, William D.; Fray, Andrew H.; Quatroche, John T.; Sturgill, Christa D. Organic Process Research and Development, 2007 , vol. 11, # 3 p. 359 - 364

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Citation Number: 37

Abstract

Described herein is the development of a control strategy resulting in exclusion of a persistent impurity (6) formed by a palladium (II)-mediated homocoupling of boronic acid (3) during a Suzuki cross-coupling reaction. Nearly complete suppression of the undesired homocoupling reaction was achieved through two process modifications. Thus, addition of a mild reducing agent, potassium formate, and use of a facile nitrogen subsurface sparge ...