A practical convergent synthesis of PI3K inhibitor GDC-0908 (<b>1</b>) is described. The process features a dihydrobenzothienooxepine formation via palladium-catalyzed intramolecular direct C-H arylation and a Negishi coupling to construct the key C-C bonds. We further developed a general synthesis of dihydrobenzothienooxepines in good to excellent yields via palladium-catalyzed intramolecular direct C-H arylation, which tolerates both electronically and sterically diverse substituents on the phenyl ring.

Convergent synthesis of PI3K inhibitor GDC-0908 featuring palladium-catalyzed direct C-H arylation toward dihydrobenzothienooxepines

2019 Fall National Meeting

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