3-chloro-4-iodo-1H-pyrazolo[3,4-b]pyridine (100 mg, 0.3578 mmol), tert-butyl 2-methyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)butylcarbamate (139.3 mg, 0.3578 mmol), Na2CO3 (536.5 μL of 2 M, 1.073 mmol) and Pd(PPh3)4 (41.35 mg, 0.03578 mmol) were placed in a microwave tube and Dioxane (1 mL) was added. The resulting suspension was stirred at 150° C. in the microwave (using a 10 minute ramp and nitrogen cooling) for 45 minutes. Reaction mixture partitioned between EtOAc and brine. The aqueous layer was extracted with EtOAc (3×20 mL) and the combined organics were dried over Na2SO4, filtered, and concentrated under reduced pressure to give a dark yellow gum. This material was purified by column chromatography (35% EtOAc in hexanes, loaded in DCM, ˜75 mL silica) to give a slightly yellow gum (68.4 mg, 46% Yield).
