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3-Bromophenol → 5-Biphenyl-4-yl-2-(3-bromo-phenoxy)-6-fluoro-1H-benzoimidazole

HRID 1960135
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HRID 1960135 반응식
[C:1]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:6]=[CH:5][C:4]([C:7]2[C:19]([F:20])=[CH:18][C:10]3[NH:11][C:12](S(C)(=O)=O)=[N:13][C:9]=3[CH:8]=2)=[CH:3][CH:2]=1.[Br:27][C:28]1[CH:29]=[C:30]([OH:34])[CH:31]=[CH:32][CH:33]=1>N1C=CC=CC=1.CCOC(C)=O>[C:1]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:6]=[CH:5][C:4]([C:7]2[C:19]([F:20])=[CH:18][C:10]3[NH:11][C:12]([O:34][C:30]4[CH:31]=[CH:32][CH:33]=[C:28]([Br:27])[CH:29]=4)=[N:13][C:9]=3[CH:8]=2)=[CH:3][CH:2]=1
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참가 물질

5

반응물 2

HCID 115633-BromophenolHCID 674455365-Biphenyl-4-yl-6-fluoro-2-methanesulfonyl-1H-benzoimidazole

생성물 1

HCID 674463835-Biphenyl-4-yl-2-(3-bromo-phenoxy)-6-fluoro-1H-benzoimidazole

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of compound 13-6 (1.53 g, 4.2 mmol) in 20 mL in pyridine was added 3-bromo-phenol (1.4 g, 8.4 mmol). The reaction mixture was heated to reflux and allowed to stir for 48 h. The reaction mixture was diluted with EtOAc (150 mL) and washed three times with 100 mL portions of saturated aqueous ammonium chloride. The combined organic layers were dried over MgSO4 filtered and concentrated in vacuo. The crude was purified on ISCO (EtOAc/Hexanes=1/1) to yield the title compound 13-7 along with recovered starting material 13-6.

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux
  3. washwashed three times with 100 mL portions of saturated aqueous ammonium chloride
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude was purified on ISCO (EtOAc/Hexanes=1/1)

출처 및 근거

ORD 기록
ord-c5406b9f3fb74ecf9963fcda22d5b0d8
출처 데이터셋
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08410284B2

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