Sodium Carbonate → HCID 66716902, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of N-[3-(5-Iodo-imidazo[2,1-b][1,3,4]thiadiazol-2-yl)-phenyl]-acetamide (0.16 g, 0.416 mmol, 1 eq), 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3-trifluoromethyl-pyridin-2-ylamine (0.12 g, 0.416 mmol, 1 eq), 2M aq Na2CO3 (0.9 mL) and PdCl2(PPh3)2 (60 mg, 0.083 mmol, 0.2 eq) in dioxane (5 mL) was heated at 110° C. for 90 min. The solvent was removed under reduced pressure and the residue was redissolved in DCM and washed with water. The organic layer was dried over Na2SO4, filtered and evaporated. The residue was purified by flash-chromatography (DCM: MeOH, 5 to 15%) and by HPLC to afford the desired product (7 mg, 4%). HPLC-MS (5-100% B in 8 min at 0.8 mL): tR=4.74 min, [M+H]+ m/z 419.1; 1H NMR (300 MHz, DMSO) δ 10.30 (s, 1H), 8.89 (s, 1H), 8.32 (m, 2H), 7.81 (m, 2H), 7.62 (d, J=7.8 Hz, 1H), 7.54 (t, J=7.9 Hz, 1H), 6.75 (s, 2H), 2.09 (s, 3H).

Provenance & Evidence