Late-stage derivatization of pharmaceutically relevant scaffolds relies on the availability of highly functional-group tolerant reactions. Reactions that increase the sp3 character of molecules enable the pursuit of more selective and well-tolerated pharmaceuticals. Herein, we report the use of sp3-sp2 cross-electrophile reductive couplings to modify a generic ATP-competitive kinase inhibitor with a broad range of primary and secondary alkyl halide coupling partners.