8-Hydroxyquinoline → 4-bromo-1-(4-(trifluoromethoxy)phenyl)-1H-imidazole

HRID 1189499Notes

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]=1

Participants

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 water, ammonium chloride (saturated), water and sodium bicarbonate. The organics were dried over MgSO4, filtered and purified on a reverse phase column 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 water, ammonium chloride (saturated), water and sodium bicarbonate
dry with materialThe organics were dried over MgSO4
filtrationfiltered
custompurified on a reverse phase column

Sources & evidence

ORD record: ord-9eb5a16a847c4f4fafa2e54540c7f8c0
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08674109B2

Reaction notes

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