Potassium Carbonate → HCID 60196594, compound

Participants

Reaction Steps

To a suspension of N-[4-(4-fluoro-2-methoxy-phenyl)-pyridin-3-yl]-3-hydroxy-N-methyl-5-trifluoromethyl-benzamide (0.06 g, 143 μmol) in acetonitrile (1 mL) were added 1-bromo-2-methoxyethane (19.8 mg, 143 μmol) and DIPEA (22.1 mg, 29.9 μL, 171 μmol) and the light yellow suspension was stirred at room temperature for 45 minutes. To the reaction mixture was added potassium carbonate (23.7 mg, 171 μmol) and stirring was continued for 2.75 hours at room temperature. Then the reaction mixture was stirred at reflux temperature for 16 hours. The reaction mixture was poured on saturated aqueous NH4Cl solution and EtOAc and the layers were separated. The aqueous layer was extracted twice with EtOAc. The organic layers were dried over MgSO4, filtered, treated with silica gel and evaporated. The product was purified by preparative HPLC (Gemini NX column) using a gradient of MeOH:water (containing 0.1% formic acid) (20:80 to 98:2). Light brown solid (0.048 g; 70%). MS (ESI): m/z=479.16 [M+H]+.

Provenance & Evidence