Ethyl Acetate → HCID 57668087, compound

HRID 2191799Notes

Reaction equation

HRID 2191799 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[CH:11]=[CH:12]/[C:13]2[CH:25]=[CH:24][C:16]([C:17]([O:19]C(C)(C)C)=[O:18])=[C:15]([NH:26][C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)[CH:14]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C(OCC)(=O)C>[C].[Pd].CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][C:13]2[CH:25]=[CH:24][C:16]([C:17]([OH:19])=[O:18])=[C:15]([NH:26][C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)[CH:14]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 68960521HCID 68960521, compound

Product 1

HCID 57668087HCID 57668087, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To the obtained tert-butyl 4-((E)-2-(3,4-dimethoxyphenyl)vinyl)-2-(4-fluoroanilino)benzoate were added ethyl acetate 1.5 mL, methanol 1.5 mL and 10% palladium-carbon 28 mg sequentially, and it was stirred under hydrogen atmosphere at room temperature for 3 hours and 30 minutes. The solvent was removed under reduced pressure after insoluble matter was filtrated. Trifluoroacetic acid 7.5 mL was added to the obtained residue, and it was stirred at room temperature for 2 hours. The solvent was removed under reduced pressure, diisopropyl ether was added to obtained residue, and solid matter was filtrated to give 4-(2-(3,4-dimethoxyphenyl)ethyl)-2-(4-fluoroanilino)benzoic acid 56 mg of a yellow solid.

Workup

  1. customThe solvent was removed under reduced pressure after insoluble matter
  2. filtrationwas filtrated
  3. additionTrifluoroacetic acid 7.5 mL was added to the obtained residue, and it
  4. stirringwas stirred at room temperature for 2 hours
  5. customThe solvent was removed under reduced pressure, diisopropyl ether
  6. additionwas added
  7. customto obtained residue, and solid matter
  8. filtrationwas filtrated

Sources & evidence

ORD record
ord-c5ef0797d9de45a98682850fa356bcb2
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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