Styrene → 2-Hydroxy-5-phenylethenyl-N-[3,5-bis(trifluoromethyl)phenyl]benzamide

HRID 1865401Notes

Reaction equation

HRID 1865401 reaction equation
[OH:1][C:2]1[CH:24]=[CH:23][C:22](I)=[CH:21][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[C:9]([C:17]([F:20])([F:19])[F:18])[CH:8]=1)=[O:5].[CH2:26]=[CH:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(NC(C)C)(C)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.CN(C)C=O>[OH:1][C:2]1[CH:24]=[CH:23][C:22]([CH:26]=[CH:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:21][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[C:9]([C:17]([F:20])([F:19])[F:18])[CH:8]=1)=[O:5]

Participants

8

Reactant 4

HCID 7501StyreneHCID 7912DiisopropylamineHCID 80271Tri-o-tolylphosphineHCID 11190699N-[3,5-bis(trifluoromethyl)phenyl]-2-hydroxy-5-iodo-benzamide

Product 1

HCID 728218852-Hydroxy-5-phenylethenyl-N-[3,5-bis(trifluoromethyl)phenyl]benzamideYield 38.3%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-hydroxy-5-iodo-N-[3,5-bis(trifluoromethyl)phenyl]-benzamide(compound of Example 81(1); 475 mg, 1 mmol), styrene (130 mg, 1.25 mmol), palladium acetate(4.5 mg, 0.02 mmol), tris(ortho-tolyl)phosphine(12.2 mg, 0.04 mmol), diisopropylamine(388 mg, 3 mmol) and N,N-dimethylformamide(2 mL) was refluxed for 8 hours. After the reaction mixture was cooled to room temperature, water was added and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water and brine, and dried over anhydrous magnesium sulfate. The residue obtained by evaporation of the solvent under reduced pressure was purified by column chromatography on silica gel(n-hexane:isopropyl ether=2:1→1:1) to give the title compound (173 mg, 38.3%) as a pale yellow solid.

Workup

  1. temperaturewas refluxed for 8 hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe residue obtained by evaporation of the solvent under reduced pressure
  6. customwas purified by column chromatography on silica gel(n-hexane:isopropyl ether=2:1→1:1)

Sources & evidence

ORD record
ord-fc39842569f44f51b9868e10f42f20ca
Source dataset
uspto-grants-2009_12
Patent number
US07626042B2

Reaction notes

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