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

HRID 644531노트

반응식

HRID 644531 반응식
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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 178418476HCID 178418476, 화합물촉매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

실험 절차

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)+.

후처리

  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)+

출처 및 근거

ORD 기록
ord-f9edc6a6408e430cb79f68f40ca709a7
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07700638B2

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