Sodium Carbonate → HCID 66717262, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-Iodo-2-(3-methanesulfonyl-phenyl)-imidazo[2,1-b][1,3,4]thiadiazole (0.091 g, 0.225 mmol, 1 eq), and 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3-trifluoromethyl-pyridin-2-ylamine (0.097 g, 0.337 mmol, 1.5 eq), PdCl2(PPh3)2 (32 mg, 0.045 mmol, 0.2 eq) and 2M Na2CO3 (1 mL) and dioxane (5 mL). The reaction mixture was heated at 110° C. for 24 h. The solvent was evaporated, the residue was 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 triturated from MeOH and filtered off. The solid was purified by column chromatography (0-5% MeOH in DCM) to give the desired product (20 mg, 20%) as a yellow solid. HPLC-MS (5-100% B in 8 min at 0.8 mL): tR=5.25 min, [M+H]+ m/z 440.0; 1H NMR (300 MHz, DMSO) δ 8.90 (d, J=1.8 Hz, 1H), 8.44 (d, J=1.6 Hz, 1H), 8.37 (d, J=2.0 Hz, 1H), 8.33 (d, J=7.9 Hz, 1H), 8.19 (d, J=8.1 Hz, 1H), 7.92 (t, J=7.9 Hz, 1H), 7.84 (s, 1H), 6.74 (s, 2H), 3.32 (s, 3H).

Provenance & Evidence