(E)-Methyl 5-fluoro-2-(3-(4-fluorophenyl)-2-(1-methyl-1H-1,2,4-triazol-5-yl)acryloyl)-3-nitrobenzoate → Methyl 7-fluoro-2-(4-fluorophenyl)-1-hydroxy-3-(1-methyl-1H-1,2,4-triazol-5-yl)-4-oxo-1,2,3,4-tetrahydroquinoline-5-carboxylate

Participants

Reaction Steps

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) (200 mg, 0.467 mmol) in methanol (20 mL) was added 10% Pd/C (24 mg). After the addition, the mixture was stirred under H2 (1 atm) at room temperature for 0.5 h. The reaction system was then filtered and evaporated under reduced pressure. The residue was purified by chromatography (ethyl acetate:petroleum ether=1:1) to give the title compound (10) (110 mg, yield 57%) as an off-white foam. LC-MS (ESI) m/z: 415 (M+H)+. 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 3.53 (s, 3H), 3.73 (s, 3H), 5.08 (d, 2H), 5.27 (d, 2H), 6.95 (dd, 1H), 7.08 (dd, 2H), 7.15 (dd, 1H), 7.42 (dd, 2H), 7.77 (s, 1H), 9.92 (s, 1H).

Provenance & Evidence