Diethyl Pyrocarbonate → 2-[ethyl-(3-fluorophenyl)sulfonyl-amino]-N-[[2-[4-(trifluoromethyl)phenyl]-4-pyridyl]methyl]prop-2-enamide

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Reaction Steps

Acid 4F (330 mg, 1.2 mmol) was dissolved in 15 ml of THF and at rt DEPC (1.3 equiv, 0.23 mL) and [2-[4-(trifluoromethyl)phenyl]-4-pyridyl]methanamine 21A (1.1 mol equiv., 335 mg) were added to the solution. The mixture was stirred at rt overnight then evaporated. The residue was dissolved in AcOEt (30 mL) and washed with water (1×20 mL) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude by chromatographic column (EtOAc 1/petroleum ether 1) afforded 100 mg of a white solid. Yield=20% 1HNMR (DMSO, 200 MHz) δ 1.09 (3H, t, J=7.2 Hz), 3.44 (2H, q, J=6.8 Hz), 4.50 (2H, d, J=6 Hz), 5.21 (1H, s), 6.14 (1H, s), 7.34 (1H, dd, J=4.8), 7.65 (m, 4H), 7.81 (d, 2H, J=7.9), 8.01 (s, 1H), 8.31 (d, 2H, J=7.8), 8.65 (d, 1H, J=5.8), 8.92 (t, 1H). [M+1] 507.62 (C24H21F4N3O3S requires 507.50).

Provenance & Evidence