A mixture of 2-(1-Ethyl-1H-pyrazol-4-yl)-5-iodo-imidazo[2,1-b][1,3,4]thiadiazole (110 mg, 0.319 mmol, 1 eq), 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3-trifluoromethyl-pyridin-2-ylamine (119 mg, 0.414 mmol, 1.3 eq), Pd(PPh3)2Cl2 (45 mg, 0.064 mmol, 0.2 eq) and 2M aq Na2CO3 (1 mL) in dioxane (3 mL) was refluxed for 2 h. The solvent was evaporated and the residue was treated with water. The suspension was filtered off and washed with Et2O. The solid was purified by column chromatography (DCM/MeOH 9:1) to afford the desired product (16 mg, 13%). HPLC-MS (5-100% B in 8 min at 0.8 mL): tR=4.62 min, [M+H]+ m/z 380.1; 1H NMR (300 MHz, DMSO) δ 8.84 (s, 1H), 8.61 (s, 1H), 8.29 (d, J=2.0 Hz, 1H), 8.08 (s, 1H), 7.74 (s, 1H), 6.72 (s, 2H), 4.24 (q, J=7.3 Hz, 2H), 1.43 (t, J=7.3 Hz, 3H).
