Sodium Carbonate → 3-[5-(6-Amino-5-trifluoromethyl-pyridin-3-yl)-imidazo[2,1-b][1,3,4]thiadiazol-2-yl]-benzamide

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Reaction Conditions

Reaction Steps

A mixture of 3-(5-Iodo-imidazo[2,1-b][1,3,4]thiadiazol-2-yl)-benzamide (70 mg, 0.18 mmol), 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3-trifluoromethyl-pyridin-2-ylamine (75 mg, 0.24 mmol), PdCl2(PPh3)2 (20 mg) and Na2CO3 (60 mg, 0.567 mmol) in dioxane (2 mL) and water (0.5 mL) was heated at 100° C. in a sealed tube for 2 h. The mixture was diluted with DCM (20 mL), washed with sat aq NaHCO3 (2×20 mL) and brine (30 mL), dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography and by HPLC to give the desired product (2 mg, 3%). HPLC-MS (5-100% B in 8 min at 0.8 mL): tR=4.26 min, [M+H]+ m/z 405.2; 1H NMR (300 MHz, DMSO) δ 8.84 (s, 1H), 8.34 (s, 1H), 8.30 (s, 1H), 8.22 (s, 1H), 8.06 (t, J=8.6 Hz, 2H), 7.75 (s, 1H), 7.66 (t, J=7.8 Hz, 1H), 7.55 (s, 1H), 6.67 (s, 2H).

Provenance & Evidence