A mixture of tert-butyl 3-(4-bromo-3-(5-fluoro-1-methylindolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-1-yl)azetidine-1-carboxylate (D32) (420 mg, 0.838 mmol), benzene sulfonamide (158 mg, 1.005 mmol), xantphos (97 mg, 0.168 mmol), diacetoxypalladium (18.81 mg, 0.084 mmol), cesium carbonate (819 mg, 2.51 mmol) in 1,4-dioxane (7 mL) was refluxed at 120° C. for 3 hours. The mixture was cooled. Water (50 mL) was added and extracted with ethyl acetate (3×50 mL). The combined organics were dried over magnesium sulfate, filtered and concentrated to give a residue which was purified on normal phase silica, eluting with ethyl acetate in cyclohexane (0-50%) to give the title compound (413 mg). LCMS (A): m/z (M+H)+ 578, C30H32FN5O4S requires 577 (acidic).
