Citric Acid → HCID 68960521, compound

HRID 2191798Notes

Reaction equation

HRID 2191798 reaction equation
Br[C:2]1[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[C:4]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH:3]=1.[CH3:23][O:24][C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][C:32]=1[O:33][CH3:34])[CH:28]=[CH2:29].C(N(CCCC)CCCC)CCC.F[B-](F)(F)F.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C.CN(C)C(=O)C>[CH3:23][O:24][C:25]1[CH:26]=[C:27](/[CH:28]=[CH:29]/[C:2]2[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[C:4]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[CH:3]=2)[CH:30]=[CH:31][C:32]=1[O:33][CH3:34]

Participants

9

Reactant 5

HCID 311Citric AcidHCID 7622TributylamineHCID 614003,4-DimethoxystyreneHCID 44558591Tri-t-butylphosphine fluoroborate2×HCID 68956988Tert-butyl 4-bromo-2-(4-fluoroanilino)benzoate

Product 1

HCID 68960521HCID 68960521, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalyst2×HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
120 °C

Procedure

To N,N-dimethylacetamide 2.0 mL solution of tert-butyl 4-bromo-2-(4-fluoroanilino)benzoate 0.10 g were added 3,4-dimethoxystyrene 0.081 mL, tributylamine 0.13 mL, palladium acetate 3.0 mg and tri-tert-butylphosphine tetrafluoroborate 2.0 mg at room temperature, and it was stirred under nitrogen atmosphere at 120° C. for 2 hours. Palladium acetate 3.0 mg and tri-tert-butylphosphine tetrafluoroborate 2.0 mg were added to it, and it was stirred at 120° C. for 2 hours. After the reaction mixture was cooled to room temperature, ethyl acetate and 10% citric acid aqueous solution were added to it. The organic layer was separated and collected,dried over anhydrous magnesium sulfate after sequential washing with 10% citric acid aqueous solution and saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [Trikonex company, Flash Tube 2008, eluent; hexane:ethyl acetate=4:1] to give tert-butyl 4-((E)-2-(3,4-dimethoxyphenyl)vinyl)-2-(4-fluoroanilino)benzoate.

Workup

  1. stirringwas stirred at 120° C. for 2 hours
  2. temperatureAfter the reaction mixture was cooled to room temperature
  3. customThe organic layer was separated
  4. washafter sequential washing with 10% citric acid aqueous solution and saturated sodium chloride aqueous solution
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-803383642a444f0cb871a1cb588b625a
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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