反应详情

To a solution of (E)-Methyl 5-fluoro-2-(3-(4-fluorophenyl)-2-(1-methyl-1H-1,2,4-triazol-5-yl)acryloyl)-3-nitrobenzoate (9) (214 mg, 0.5 mmol) in methanol (5 mL) was added concentrated HCl solution (w/w 37%, 1 mL), then reductive Fe powder (140 mg, 2.5 mmol) was added slowly to the reaction system. After the addition was complete the resulting mixture was refluxed for 24 hours. The reaction mixture was then filtered, concentrated, neutralized with saturated NaHCO3 (20 mL), and extracted with ethyl acetate (10 mL×3). The residue was purified by chromatography (ethyl acetate:petroleum ether=1:1) to give the title compound (5) (30 mg, yield 15%) as an off-white foam. LC-MS (ESI) m/z: 399 (M+H)+. 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 3.56 (s, 3H), 3.86 (s, 3H), 7.02 (dd, 2H), 7.21 (dd, 2H), 7.90 (s, 1H), 8.08 (s, 1H), 8.26 (dd, 1H), 8.56 (dd, 1H).

1. additionAfter the addition
2. temperaturewas refluxed for 24 hours
3. filtrationThe reaction mixture was then filtered
4. concentrationconcentrated
5. extractionextracted with ethyl acetate (10 mL×3)
6. customThe residue was purified by chromatography (ethyl acetate:petroleum ether=1:1)