(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

HRID 1617270Notes

Reaction equation

HRID 1617270 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N+:29]([O-])=[O:30])[C:5]([C:12](=[O:28])/[C:13](/[C:22]2[N:26]([CH3:27])[N:25]=[CH:24][N:23]=2)=[CH:14]/[C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]>CO.[Pd]>[F:1][C:2]1[CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[C:5]2[C:12](=[O:28])[CH:13]([C:22]3[N:26]([CH3:27])[N:25]=[CH:24][N:23]=3)[CH:14]([C:15]3[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=3)[N:29]([OH:30])[C:4]=2[CH:3]=1

Participants

4

Reactant 1

HCID 53353703(E)-Methyl 5-fluoro-2-(3-(4-fluorophenyl)-2-(1-methyl-1H-1,2,4-triazol-5-yl)acryloyl)-3-nitrobenzoate

Product 1

HCID 53353612Methyl 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-carboxylateYield 57%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

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).

Workup

  1. additionAfter the addition
  2. filtrationThe reaction system was then filtered
  3. customevaporated under reduced pressure
  4. customThe residue was purified by chromatography (ethyl acetate:petroleum ether=1:1)

Sources & evidence

ORD record
ord-9d138ee6b04348828e86826df295a492
Source dataset
uspto-grants-2014_07
Patent number
US08765945B2

Reaction notes

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