Development of a Robust Pd-Catalyzed C–S Coupling for the Synthesis of Janus Kinase Inhibitor GDC-9918
Derek M. Dalton,
Juno Castillo Siu,
Marcelino Varona-Ortiz
et al.
Abstract:The development of an in situ formed (Xantphos)Pd oxidative addition complex made possible a robust, scalable C− S coupling of a functionalized aryl bromide with 2-mercaptoethanol that ultimately enabled the synthesis of Janus Kinase inhibitor GDC-9918 on a kilogram scale. An insoluble, catalytically inactive, [12]metallacrown-6 palladium(II) complex, [Pd 6 (μ 2 -SCH 2 CH 2 OH) 12 ], was found to form quickly under most reaction conditions in the presence of 2-mercaptoethanol and a Pd catalyst and required up … Show more
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