Water → 4-Bromo-2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazole

HRID 1661884노트

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HRID 1661884 반응식
[Br:1][C:2]1[C:10]2[N:9]=[C:8]([C:11]3[CH:16]=[CH:15][C:14]([CH:17]([CH3:19])[CH3:18])=[CH:13][CH:12]=3)[NH:7][C:6]=2[C:5]([O:20][CH3:21])=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:25][CH2:26][O:27][CH3:28].O>CN(C=O)C>[Br:1][C:2]1[C:10]2[N:9]=[C:8]([C:11]3[CH:16]=[CH:15][C:14]([CH:17]([CH3:19])[CH3:18])=[CH:13][CH:12]=3)[N:7]([CH2:25][CH2:26][O:27][CH3:28])[C:6]=2[C:5]([O:20][CH3:21])=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 577720154-bromo-2-(4-isopropyl-phenyl)-7-methoxy-1H-benzoimidazole

생성물 1

HCID 112811194-Bromo-2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazole수율 563.9%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

To a stirred solution of 500 mg (1.45 mmol) 4-bromo-2-(4-isopropyl-phenyl)-7-methoxy-1H-benzoimidazole in 11 ml DMF, NaH (38 mg, 1.6 mmol) is added and stirring is continued for 1 h at RT, and then the reaction mixture is heated to 60° C. 0.152 ml (0.175 mmol) (2-bromoethyl)-methyl ether is added and stirring is continued at this temperature for another 6 h. The reaction mixture is cooled to room temperature, poured into water and extracted (3×) with ethyl acetate. The combined organic layers are washed with water (2×) and brine, dried over MgSO4, filtered and concentrated in vacuo. The residue is purified by flash-chromatography on silica gel (hexane:EtOAc=3:1) to afford 398 mg of the title compound as colorless oil.

후처리

  1. stirringstirring
  2. waitis continued at this temperature for another 6 h
  3. temperatureThe reaction mixture is cooled to room temperature
  4. extractionextracted (3×) with ethyl acetate
  5. washThe combined organic layers are washed with water (2×) and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue is purified by flash-chromatography on silica gel (hexane:EtOAc=3:1)

출처 및 근거

ORD 기록
ord-faba9025e5e64145b6850c1c74659af8
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08030497B2

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