A glass tube was charged with 4′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1′-biphenyl]-2-ol (73.5 mg, 0.25 mmol), 5-bromo-6-fluoro-1H-indole-3-carbaldehyde (60 mg, 0.25 mmol), toluene (1.2 mL), THF (0.6 mL), EtOH (0.6 mL), and 2.0 M potassium carbonate solution (0.6 mL, 1.2 mmol). Nitrogen was then bubbled through the mixture for 5 minutes then [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (21.5 mg, 0.025 mmol) was added. The tube was sealed and heated to 115° C. for 2 hours. The reaction was cooled to room temperature, opened, and neutralized with 1.0 M sodium hydrogensulfate then diluted with ethyl acetate. The layers were separated and the aqueous extracted with ethyl acetate (×2). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was dissolved in methylene chloride and methanol, silica was added, and the solvent removed in vacuo. The dry-loaded silica gel was then subjected to flash column chromatography (20% to 100% ethyl acetate/heptane) to provide the title compound as a white solid (20 mg, 24%). MS (ES+) 332.3 (M+H). 1H NMR (500 MHz, DMSO-d6) δ ppm 12.24 (br. s, 1 H) 9.96 (s, 1 H) 9.59 (s, 1 H) 8.36 (s, 1 H) 8.19 (d, 1 H) 7.67 (d, 2 H) 7.58 (d, 2 H) 7.46 (d, 1 H) 7.33 (d, 1 H) 7.18 (t, 1 H) 6.97 (d, 1 H) 6.91 (t, 1 H).
