Iodoethane → 4-Ethyl-2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazole

HRID 1661896Notes

Reaction equation

Br[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]([CH2:20][CH2:21][O:22][CH3:23])[C:6]=2[C:5]([O:24][CH3:25])=[CH:4][CH:3]=1.[CH2:26](I)[CH3:27]>C1COCC1.C([Li])(C)(C)C>[CH2:26]([C:2]1[C:10]2[N:9]=[C:8]([C:11]3[CH:12]=[CH:13][C:14]([CH:17]([CH3:19])[CH3:18])=[CH:15][CH:16]=3)[N:7]([CH2:20][CH2:21][O:22][CH3:23])[C:6]=2[C:5]([O:24][CH3:25])=[CH:4][CH:3]=1)[CH3:27]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 150 mg (0.223 mmol) 4-bromo-2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazole in 8 ml THF, 0.289 ml tert-butyllithium (1.7M in pentane) is slowly added at −78° C. This mixture is stirred for 1 h at −78° C. then 54 μl (0.669 mmol) ethyl iodide is added. The reaction mixture is warmed to room temperature and stirring is continued for 12 h. The reaction mixture is cooled to room temperature, poured on 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=2:1) to afford 25 mg of the title compound as a colorless oil.

Workup

temperatureThe reaction mixture is warmed to room temperature
stirringstirring
waitis continued for 12 h
temperatureThe reaction mixture is cooled to room temperature
additionpoured on water
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=2:1)

Sources & evidence

ORD record: ord-8bdb2edf428240969d754821a313a2d6
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08030497B2

Reaction notes

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