To a mixture of 2-bromo-5-iodoimidazo[2,1-b][1,3,4]thiadiazole (0.150 g, 0.455 mmol), 3-cyanophenylboronic acid (0.477 mmol) and PdCl2(Ph3P)2 (0.064 g) in dioxane (3 mL), an aq. solution of Na2CO3(2 M, 0.9 mL) was added. The reaction mixture was heated at 110° C. for 24 h in a sealed tube. The solvent was evaporated, the residue precipitated with water, and after drying the resulting gum was washed with Et2O. The residue was suspended in dioxane (3 mL), and 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3-trifluoromethyl-pyridin-2-ylamine (1.05 eq), PdCl2(Ph3P)2 (0.2 eq) and a sat. aq. solution of K2CO3 (0.9 mL) were added. The reaction mixture was heated at 100° C. for 16 h and then concentrated to dryness. The residue was washed with water, followed by ethyl ether. The resulting solid was washed with DCM followed by MeOH. The DCM filtrate was evaporated and purified by HPLC to yield the desired product (0.10 g). HPLC-MS: (5-100% B in 8 min, 0.8 mL/min, 50° C.): tR=5.15 min, [M+H]+ m/z 387.1; 1H NMR (300 MHz, DMSO-d6) δ 8.90 (s, 1H), 8.49 (s, 1H), 8.38-8.25 (m, 2H), 8.12 (d, J=7.9 Hz, 1H), 7.92-7.74 (m, 2H), 6.75 (s, 2H) ppm.
