Sodium Carbonate → 5-{2-[4-(Morpholine-4-sulfonyl)-phenyl]-imidazo[2,1-b][1,3,4]thiadiazol-5-yl}-3-trifluoromethyl-pyridin-2-ylamine

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Reaction Conditions

Reaction Steps

A mixture of 5-Iodo-2-[4-(morpholine-4-sulfonyl)-phenyl]-imidazo[2,1-b][1,3,4]thiadiazole (85 mg, 0.18 mmol), 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3-trifluoromethyl-pyridin-2-ylamine (60 mg, 0.27 mmol), PdCl2(PPh3)2 (26 mg, 0.037 mmol) and 2M aq Na2CO3 (0.5 mL) in dioxane (4 mL) was heated at 90° C. for 18 h. On cooling, the solvents were removed in vacuo and the residue was triturated from EtOAc and filtered off. The filtrate was evaporated and the residue was recrystallyzed from MeOH, filtered and washed with water. The solid was purified by column chromatography (DCM/MeOH) to afford the desired product (31 mg, 34%) as a yellow solid. HPLC-MS (5-100% B in 8 min at 0.8 mL): tR=5.12 min, [M+H]+ m/z 511.2; 1H NMR (300 MHz, DMSO) δ 8.89 (s, 1H), 8.36 (s, 1H), 8.26 (d, J=8.3 Hz, 2H), 7.97 (d, J=8.3 Hz, 2H), 7.84 (s, 1H), 6.77 (s, 2H), 3.65 (s, 4H), 2.95 (s, 4H).

Provenance & Evidence