A mixture of 5-bromo-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 42.1, 5 g, 13.85 mmol), 3-pyridylboronic acid (1.872 g, 15.23 mmol), PdCl2(dppf) (0.507 g, 0.692 mmol), K3PO4 (8.82 g, 41.5 mmol), EtOH (9.33 mL), water (14 mL) and toluene (70 mL) was stirred at 100° C. for 2 h. The solvent was evaporated off under reduced pressure and the residue was treated with water and extracted with EtOAc. The combined extracts were washed with water and brine, dried over Na2SO4 and the solvent was evaporated off under reduced pressure. The residue was purified by flash chromatography (Silica gel column, 500 g, EtOAc/MeOH from 0 to 2% MeOH). Fractions containing the pure product were combined and the solvent was evaporated off under reduced pressure to give a residue which was dissolved in THF, stirred overnight with Si-Thiol (1 g), filtered and the filtrate was evaporated off under reduced pressure to give the title compound as a white solid. UPLC-MS (Condition 7) tR 0.95 min, m/z=358 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 7.41 (d, J=8.56 Hz, 2H) 7.59 (dd, J=7.95, 4.77 Hz, 1H) 7.91 (m, J=9.00 Hz, 2H) 8.29 (dt, J=7.83, 1.96 Hz, 1H) 8.65 (t, J=2.20 Hz, 1H) 8.68 (dd, J=4.77, 1.59 Hz, 1H) 9.08 (d, J=1.96 Hz, 1H) 9.13 (d, J=1.96 Hz, 1H) 9.16 (d, J=2.20 Hz, 1H) 10.69 (s, 1H).
