Sodium Hydroxide → N-[4-(4-Fluoro-2-methoxy-phenyl)-pyridin-3-yl]-3-methanesulfonyl-N-methyl-5-trifluoromethoxy-benzamide

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Reaction Steps

To a solution of L-proline (18.4 mg, 160 μmol) in DMSO (2 mL) was added sodium hydroxide (6.41 mg, 160 μmol) and the turbid mixture was stirred at room temperature for 30 minutes. This mixture was added to 3-bromo-N-[4-(4-fluoro-2-methoxy-phenyl)-pyridin-3-yl]-N-methyl-5-trifluoromethoxy-benzamide (0.1 g, 200 μmol) and the resulting suspension was treated with copper(I)iodide (30.5 mg, 160 μmol) and sodium methanesulfinate (164 mg, 1.6 mmol). The reaction mixture was heated to 120° C. for 19 hours. After cooling down to room temperature 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 washed with brine, dried over MgSO4, filtered, treated with silica gel and evaporated. The compound was purified by silica gel chromatography on a 10 g column using an MPLC system eluting with a gradient of n-heptane:EtOAc (100:0 to 0:100). Colorless foam (0.065 g; 65%). MS (ESI): m/z=499.09 [M+H]+.

Provenance & Evidence