Sodium Carbonate → HCID 66717020, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-(5-Iodo-imidazo[2,1-b][1,3,4]thiadiazol-2-yl)-1H-indole (0.091 g, 0.247 mmol, 1 eq), 5-(4,4,5,5-tetramethyl[-1,3,2]dioxaborolan-2-yl)-3-trifluoromethyl-pyridin-2-ylamine (0.107 g, 0.371 mmol, 1.5 eq), 2M aq Na2CO3 (1 mL) and PdCl2(PPh3)2 (0.035 g, 0.049 mmol, 0.2 eq) in dioxane (5 mL) was heated at 110° C. for 24 h. The solvent was removed in vacuo, redissolved in DCM/water (150 mL) and extacted with DCM (2×80 mL). The organic layer was dried (MgSO4), filtered and evaporated. The residue was purified by column chromatography (0-10% MeOH in DCM and a second column 0-5% MeOH in DCM) to afford the desired product (12 mg, 12%) as a yellow solid. HPLC-MS (5-100% B in 8 min at 0.8 mL): tR=5.08 min, [M+H]+ m/z 401.0; 1H NMR (300 MHz, DMSO) δ 11.57 (s, 1H), 8.90 (d, J=1.8 Hz, 1H), 8.39 (d, J=2.1 Hz, 1H), 8.20 (d, J=1.6 Hz, 1H), 7.75 (s, 1H), 7.73 (dd, J=9.2, 2.4 Hz, 1H), 7.61 (d, J=8.6 Hz, 1H), 7.52 (m, 1H), 6.73 (s, 2H), 6.64 (s, 1H).

Provenance & Evidence