Diethyl Pyrocarbonate → 2-[ethyl-(4-fluorophenyl)sulfonyl-amino]-N-[[2-methoxy-6-[4-(trifluoromethyl)phenyl]-4-pyridyl]methyl]prop-2-enamide

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Reaction Steps

A solution of acid 4B (0.31 g, 1.1 mmol) in THF (20 mL) was added with DEPC (0.22 mL, 1.3 mol eq) and the mixture was stirred at room temperature several minutes. Then [2-methoxy-6-[4-(trifluoromethyl)phenyl]-4-pyridyl]methanamine 27I (0.36 g, 1.1 mol eq) and a catalytic amount of TEA were added, then the reaction mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure, water was added to the residue that is extracted with EtOAc (3×30 mL) and washed with brine (1×40 mL). The separated organic phase was dried over Na2SO4, evaporated to dryness and the residue was purified by flash chromatography (1/1 EtOAc/Petroleum ether) to afford a white solid (180 mg) after crystallization from ethyl ether. Yield=30%. 1HNMR (DMSO, 200 MHz) δ 1.08 (t, 3H, J=6), 3.39 (m, 2H), 3.95 (s, 3H), 4.45 (d, 2H, J=6.2), 5.14 (s, 1H), 6.13 (s, 1H), 6.79 (s, 1H), 7.47 (t, 2H, J=8.2), 7.64 (s, 1H), 7.85 (m, 4H), 8.31 (d, 2H, J=7.8), 8.84 (bt, 1H). [M+1] 537.05 (C25H23F4N3O4S requires 537.53).

Provenance & Evidence