To a solution of 2-[4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl]-2-methylpropan-1-ol (102 mg, 0.386 mmol) and 5-bromo-4,6-difluoro-1H-indole-3-carbaldehyde (100 mg, 0.386 mmol) in toluene (6 mL) and EtOH (2 mL) was added a solution of potassium carbonate (160 mg, 1.159 mmol) in water (1.0 mL) and Pd(dppf)Cl2 (15.8 mg, 0.019 mmol) at room temperature under N2. The reaction was cooled to room temperature, and extracted with ethyl acetate (10 mL×2). The organic layers were washed with brine (10 mL), and dried over sodium sulfate and concentrated to give a crude residue, which was purified by column chromatography to give the title compound (40 mg, 32%) as a yellow solid. 1H NMR (400 MHz, CD3OD) δ 10.0 (s, 1H), 8.13 (s, 1H), 7.51 (d, 2H), 7.40 (d, 2H), 7.19 (d, 1H), 3.63 (s, 2H), 1.36 (s, 6H).
