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

HRID 1960135Notes

Reaction equation

HRID 1960135 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-c5406b9f3fb74ecf9963fcda22d5b0d8
Source dataset
uspto-grants-2013_04
Patent number
US08410284B2

Reaction notes

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