Methyl iodide → benzyl {2-(4-bromophenyl)-1-[5-(2,2-dimethylbutyl)-1-methyl-1H-imidazol-2-yl]ethyl}methylcarbamate

HRID 425391Notes

Reaction equation

[H-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH:11]([NH:24][C:25](=[O:34])[O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:12]2[N:13]([CH3:23])[C:14]([CH2:17][C:18]([CH3:22])([CH3:21])[CH2:19][CH3:20])=[CH:15][N:16]=2)=[CH:6][CH:5]=1.[CH3:35]I>O1CCCC1>[Br:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH:11]([N:24]([CH3:35])[C:25](=[O:34])[O:26][CH2:27][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:12]2[N:13]([CH3:23])[C:14]([CH2:17][C:18]([CH3:21])([CH3:22])[CH2:19][CH3:20])=[CH:15][N:16]=2)=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Sodium hydride (60 wt % in mineral oil) (20 mg, 0.47 mmol) was added to a solution of benzyl {2-(4-bromophenyl)-1-[5-(2,2-dimethylbutyl)-1-methyl-1H-imidazol-2-yl]ethyl}carbamate (70 mg, 0.14 mmol) in tetrahydrofuran. After stirring at 0° C. for 10 min, methyl iodide (20 μL, 0.31 mmol) was added and the reaction allowed to warm to ambient temperature. The reaction mixture was quenched with water and extracted with ethyl acetate. The combined organic extracts were dried (magnesium sulfate) and concentrated in vacuo to afford benzyl {2-(4-bromophenyl)-1-[5-(2,2-dimethylbutyl)-1-methyl-1H-imidazol-2-yl]ethyl}methylcarbamate which was used in the subsequent step without further purification.

Workup

temperatureto warm to ambient temperature
customThe reaction mixture was quenched with water
extractionextracted with ethyl acetate
dry with materialThe combined organic extracts were dried (magnesium sulfate)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-a46c91d3761844ac9b93f336a2a6f44b
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08106070B2

Reaction notes

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