1,3-Propanediol → 7-(3-Acetylphenyl)-1-phenyl-5-trifluoromethylbenzimidazole

HRID 644531ノート

反応式

HRID 644531 の反応式
I[C:2]1[C:7]2[N:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:9]=[N:10][C:6]=2[CH:5]=[C:4]([C:17]([F:20])([F:19])[F:18])[CH:3]=1.[C:21]([C:24]1[CH:25]=[C:26](B(O)O)[CH:27]=[CH:28][CH:29]=1)(=[O:23])[CH3:22].C(O)CCO.C(=O)([O-])[O-].[K+].[K+]>C(COC)OC.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:21]([C:24]1[CH:29]=[C:28]([C:2]2[C:7]3[N:8]([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)[CH:9]=[N:10][C:6]=3[CH:5]=[C:4]([C:17]([F:20])([F:19])[F:18])[CH:3]=2)[CH:27]=[CH:26][CH:25]=1)(=[O:23])[CH3:22]

参加物

8

反応物 4

HCID 104421,3-PropanediolHCID 11430Potassium CarbonateHCID 27343103-Acetylphenylboronic acidHCID 194260247-Iodo-1-phenyl-5-(trifluoromethyl)-1H-benzimidazole

生成物 1

HCID 114289357-(3-Acetylphenyl)-1-phenyl-5-trifluoromethylbenzimidazole

試薬・触媒・溶媒 3

HCID 178418476HCID 178418476、化合物触媒HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

A mixture of 7-iodo-1-phenyl-5-trifluoromethylbenzimidazole (7.38 g, 19 mmol), 3-acetylphenyl boronic acid (4.67 g, 28.5 mmol), 1,3-propanediol (6.8 ml, 95 mmol), potassium carbonate (13.1 g, 95 mmol) and bis(triphenylphosphin)palladium dichloride (200 mg, 0.28 mmol) in a mixture of dimethoxyethane (60 ml) and water (30 ml) was stirred at reflux in a nitrogen atmosphere for 1 hour. The cooled reaction mixture was filtered through a pad of Celite and the filter was rinsed with ethyl acetate. The organic layer was collected, dried over magnesium sulphate and concentrated under reduced pressure. The title product precipitated upon addition of diethyl ether to the concentrate (6.17 g, 85%) m/z, 381.1 (M+H)+.

後処理

  1. temperatureat reflux in a nitrogen atmosphere for 1 hour
  2. customThe cooled reaction mixture
  3. filtrationwas filtered through a pad of Celite
  4. washthe filter was rinsed with ethyl acetate
  5. customThe organic layer was collected
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated under reduced pressure
  8. customThe title product precipitated upon addition of diethyl ether to the
  9. concentrationconcentrate (6.17 g, 85%) m/z, 381.1 (M+H)+

出典と根拠

ORDレコード
ord-f9edc6a6408e430cb79f68f40ca709a7
出典データセット
uspto-grants-2010_04
特許番号
US07700638B2

反応ノート

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