3-Bromo-1-(4-(perfluoroethoxy)phenyl)-1H-1,2,4-triazole (1.5 g, 4.2 mmol) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (1.12 g, 5.12 mmol), Pd(PPh3)4 (0.49 g, 0.424 mmol) and K2CO3 (1.17 g, 8.52 mmol) were combined in a round bottom flask in 5:1 DME/water (22 mL), and the solution was degassed with nitrogen for 15 min. The reaction was then heated for 18 h at 120° C. The reaction mixture was cooled and diluted with EtOAc and water. The layers were separated and the aqueous layer was extracted with EtOAc (2×50 ml). The combined organic extracts were dried over anhydrous MgSO4 and concentrated onto 8 g of Celite®. The Celite® was loaded onto a silica column and the target molecule was eluted using 0-100% EtOAc/hexanes to afford the title compound as a tan solid (1.13 g, 68%): 1H NMR (400 MHz, CDCl3) δ 8.52 (s, 1H), 7.99 (d, J=8.7 Hz, 2H), 7.78 (d, J=9.1 Hz, 2H), 7.36 (d, J=9.1 Hz, 2H), 6.76 (d, J=8.7 Hz, 2H), 3.90 (s, 2H); ESIMS m/z 371.2 ([M+H]+).
