To a stirred solution of 4-bromo-3-iodo-1-methyl-1H-pyrrolo[2,3-b]pyridine (D7) (5 g, 14.84 mmol) and 1-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indoline (4.61 g, 17.81 mmol) in ACN (40 mL), DMF (40 mL) and DCM (20 mL) was added 2M sodium carbonate aq. solution (74.2 mL, 148 mmol). Bis(triphenylphosphine)palladium(II) chloride (1.250 g, 1.781 mmol) was then added to the solution and the resulting mixture was heated at 55° C. for ca. 1.5 hour. The reaction mixture was diluted with DCM (100 mL) and water (150 mL). The organic phase was separated and the aqueous phase was further extracted with DCM (100 mL×3). The combined organics were dried and concentrated. The residue was purified by chromatography on silica, eluting with a gradient of 0-20% ethyl acetate in cyclohexane. The corresponding fractions were combined and concentrated to give the title compound (2.48 g). LCMS (A): m/z (M+H)+ 342/344, C17H16BrN3 requires 341/343 (acidic).
