To a mixture of 3-iodo-5-(pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-c]pyridine (GCP-P3-205-1) (200 mg, 0.44 mmol) and 2-fluoro-6-(tributylstannyl)pyridine (206 mg, 0.53 mmol) in 3 mL DMF, was added TEA 1 mL, LiCl (56 mg, 1.32 mmol) and CuI (84 mg, 0.44 mmol), and Pd(PPh3)4 (254 mg, 0.22 mmol). The reaction mixture was heated at 120° C. under microwave irradiation for 1 h, and the reaction was monitored by LCMS. Upon completion, the reaction mixture was extracted with 100 mL EtOAc, washed with 50 mL brine, and dried. The solvent was distilled off and the crude material was purified via flash chromatography, eluting with 5% to 30% ethyl acetate in heptane to afford 3-(6-fluoropyridin-2-yl)-5-(pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-c]pyridine as a yellow solid (148 mg, 80%). ESI MS m/z=421.1 (M+1).
