A solution of 147 mg (0.51 mmol) of 3-chloro-5-(2-chloro-5-ethynylphenoxy)benzonitrile, 166 mg (0.48 mmol) of tert-butyl 3-iodo-1H-pyrazolo[3,4-b]pyridine-1-carboxylate, 17 mg (0.03 mmol) of bis(triphenylphosphino)palladium (II) chloride, and 9.00 mg (0.05 mmol) of CuI in 2.5 mL DMF/5 mL triethylamine under nitrogen was stirred at room temperature for one hour. The reaction mixture was concentrated in vacuo to a dark oil. The crude oil was purified by flash chromatography over silica gel with 2.5:1 hexanes/EtOAc to provide the desired product as a yellow oil/foam. M+=405 (M−100, loss of Boc). 1H NMR (CDCl3): 1.75 (s, 9H), 7.10 (m, 1H), 7.19 (m, 1H), 7.36 (m, 1H), 7.39 (m, 2H), 7.50 (dd, 1H), 7.56 (dd, 1H), 8.21 (dd, 1H), 8.82 (dd, 1H).
