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

HRID 1661884Notes

Reaction equation

[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

Participants

Conditions

Temperature: 60 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-faba9025e5e64145b6850c1c74659af8
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08030497B2

Reaction notes

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