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

HRID 1865401노트

반응식

HRID 1865401 반응식
[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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-fc39842569f44f51b9868e10f42f20ca
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07626042B2

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