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

HRID 2384356ノート

反応式

HRID 2384356 の反応式
[F:1][C:2]([F:25])([F:24])[C:3]1[CH:4]=[C:5]([NH:13][C:14](=[O:23])[C:15]2[CH:20]=[C:19](I)[CH:18]=[CH:17][C:16]=2[OH:22])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[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>[F:1][C:2]([F:25])([F:24])[C:3]1[CH:4]=[C:5]([NH:13][C:14](=[O:23])[C:15]2[CH:20]=[C:19]([CH:26]=[CH:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH:18]=[CH:17][C:16]=2[OH:22])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

A mixture of N-[3,5-bis(trifluoromethyl)phenyl]-2-hydroxy-5-iodo-benzamide (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 cooling, water was added to the reaction mixture, and it was extracted with ethyl acetate. After the ethyl acetate layer was washed with water and brine, dried over anhydrous magnesium sulfate and concentrated, the residue was purified by column chromatography on silica gel (hexane-isopropyl ether:2/1→1/1) to give the title compound (173 mg, 38.3%) as a pale yellow solid.

後処理

  1. temperaturewas refluxed for 8 hours
  2. temperatureAfter cooling
  3. extractionwas extracted with ethyl acetate
  4. washAfter the ethyl acetate layer was washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customthe residue was purified by column chromatography on silica gel (hexane-isopropyl ether:2/1→1/1)

出典と根拠

ORDレコード
ord-e2b23fa634894b648e1dc0987c452757
出典データセット
uspto-grants-2012_09
特許番号
US08263657B2

反応ノート

読み込み中…