Benzyl Bromide → HCID 59145924, compound

HRID 887751Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:20])[CH2:4][CH2:5][C:6]1[CH:7]=[CH:8][C:9]2[N:13]=[C:12]([CH3:14])[NH:11][C:10]=2[C:15]=1[C:16]([O:18][CH3:19])=[O:17].C(=O)([O-])[O-].[K+].[K+].[CH2:27](Br)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C(#N)C.C(=O)([O-])O.[Na+]>[CH2:27]([N:13]1[C:9]2[CH:8]=[CH:7][C:6]([CH2:5][CH2:4][C:3]([O:2][CH3:1])=[O:20])=[C:15]([C:16]([O:18][CH3:19])=[O:17])[C:10]=2[N:11]=[C:12]1[CH3:14])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of methyl 6-(3-methoxy-3-oxopropyl)-2-methyl-1H-benzimidazole-7-carboxylate (417 mg, 1.51 mmol) in acetonitrile (15 mL) were added potassium carbonate (62.6 mg, 0.453 mmol) and benzyl bromide (269 μL, 2.26 mmol), and the mixture was stirred at 80° C. for 3 hr. The reaction solution was diluted with saturated aqueous sodium hydrogen carbonate solution, extracted with ethyl acetate, washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (methanol/ethyl acetate=0/100→5/95) to give the title compound (164 mg, yield 30%).

Workup

extractionextracted with ethyl acetate
washwashed with water and saturated brine
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel column chromatography (methanol/ethyl acetate=0/100→5/95)

Sources & evidence

ORD record: ord-4701104a051941cd93e6356be5e16e11
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08247429B2

Reaction notes

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