tert-butyl 2-(4-fluoroanilino)-4-((E)-2-(2-methoxyphenyl)vinyl)benzoate → Tert-butyl 2-(4-fluoroanilino)-4-(2-(2-methoxyphenyl)ethyl)benzoate

HRID 2191801Notes

Reaction equation

HRID 2191801 reaction equation
[F:1][C:2]1[CH:31]=[CH:30][C:5]([NH:6][C:7]2[CH:19]=[C:18](/[CH:20]=[CH:21]/[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[O:28][CH3:29])[CH:17]=[CH:16][C:8]=2[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[CH:4][CH:3]=1>[C].[Pd].C(O)(=O)C>[F:1][C:2]1[CH:31]=[CH:30][C:5]([NH:6][C:7]2[CH:19]=[C:18]([CH2:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[O:28][CH3:29])[CH:17]=[CH:16][C:8]=2[C:9]([O:11][C:12]([CH3:13])([CH3:15])[CH3:14])=[O:10])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 68962915tert-butyl 2-(4-fluoroanilino)-4-((E)-2-(2-methoxyphenyl)vinyl)benzoate

Product 1

HCID 68960995Tert-butyl 2-(4-fluoroanilino)-4-(2-(2-methoxyphenyl)ethyl)benzoate

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalyst2×HCID 176Acetic AcidSolvent

Procedure

To the obtained tert-butyl 2-(4-fluoroanilino)-4-((E)-2-(2-methoxyphenyl)vinyl)benzoate were added acetic acid 4.0 mL and 10% palladium-carbon 26 mg sequentially, and it was stirred under hydrogen atmosphere at room temperature for 7 hours. Subsequently, 10% palladium-carbon 39 mg was added to it, it was stirred under hydrogen atmosphere at the same temperature for 3 hours, subsequently it was stirred at 40° C. for 2 hours. After the reaction mixture was cooled to room temperature, insoluble matter was filtrated, 10% palladium-carbon 64 mg was added to it, and it was stirred under hydrogen atmosphere at 40° C. for 3 hours and 30 minutes. After the reaction mixture was cooled to room temperature, insoluble matter was filtrated, and the solvent was removed under reduced pressure. To the obtained residue were added water, ethyl acetate and saturated sodium hydrogen carbonate aqueous solution. The organic layer was separated and collected,dried over anhydrous magnesium sulfate after washing with saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure to give tert-butyl 2-(4-fluoroanilino)-4-(2-(2-methoxyphenyl)ethyl)benzoate 0.11 g of a pale red oil.

Workup

  1. stirringwas stirred under hydrogen atmosphere at the same temperature for 3 hours
  2. stirringsubsequently it was stirred at 40° C. for 2 hours
  3. temperatureAfter the reaction mixture was cooled to room temperature
  4. filtrationinsoluble matter was filtrated
  5. addition10% palladium-carbon 64 mg was added to it, and it
  6. stirringwas stirred under hydrogen atmosphere at 40° C. for 3 hours and 30 minutes
  7. temperatureAfter the reaction mixture was cooled to room temperature
  8. filtrationinsoluble matter was filtrated
  9. customthe solvent was removed under reduced pressure
  10. additionTo the obtained residue were added water, ethyl acetate and saturated sodium hydrogen carbonate aqueous solution
  11. customThe organic layer was separated
  12. washafter washing with saturated sodium chloride aqueous solution
  13. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-cc44e88a8ddd4bd8bf023f8d0b28540f
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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