8-Hydroxyquinoline → 4-bromo-1-(4-(trifluoromethoxy)phenyl)-1H-imidazole
Reaction equation
[Br:1][C:2]1[N:3]=[CH:4][NH:5][CH:6]=1.OC1C=CC=C2C=1N=CC=C2.C(=O)([O-])[O-].[Cs+].[Cs+].[F:24][C:25]([F:35])([F:34])[O:26][C:27]1[CH:32]=[CH:31][C:30](I)=[CH:29][CH:28]=1>CCOC(C)=O.[Cu]I.O.CN(C=O)C>[Br:1][C:2]1[N:3]=[CH:4][N:5]([C:30]2[CH:29]=[CH:28][C:27]([O:26][C:25]([F:24])([F:34])[F:35])=[CH:32][CH:31]=2)[CH:6]=1Participants
9
Reactant 4
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 130 °C
Procedure
A round bottom flask was charged with 4-bromoimidazole (1.15 g, 7.81 mmol), CuI (0.07 g, 0.36 mmol), 8-hydroxyquinoline (0.05 g, 0.36 mmol), cesium carbonate (3.39 g, 10.4 mmol) and 4-trifluoromethoxyiodobenzene (1.50 g, 5.21 mmol). A 10:1 mixture of DMF (15 mL) and H2O (1.5 mL) was added to the reaction mixture, and the solution was heated to 130° C. for 4 h. The reaction mixture was then diluted with EtOAc and washed sequentially with H2O, ammonium chloride (NH4Cl, saturated), H2O and sodium bicarbonate (NaHCO3). The organics were dried over MgSO4, filtered and purified by reverse phase column chromatography to give the imidazole (820 mg) as a white solid: mp 139-141° C.; ESIMS m/z 308.0 (M+H).
Workup
- additionwas added to the reaction mixture
- washwashed sequentially with H2O, ammonium chloride (NH4Cl, saturated), H2O and sodium bicarbonate (NaHCO3)
- dry with materialThe organics were dried over MgSO4
- filtrationfiltered
- custompurified by reverse phase column chromatography
Sources & evidence
- ORD record
- ord-ff065cca4b164695b603c70faad64bfd
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08680269B2
Reaction notes
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