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

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Reaktionsgleichung

[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

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag: ord-ec818460c4d24322b427a0bc9a4f95bc
Quelldatensatz: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08318767B2

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