Benzyl Bromide → HCID 58027019, Verbindung

HRID 1966298Notizen

Reaktionsgleichung

[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:32])=[C:6]([CH:31]=1)[O:7][CH2:8][C:9]1[C:18]([C:19]2[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][C:20]=2[O:26][CH3:27])=[CH:17][CH:16]=[C:15]2[C:10]=1[C:11]([CH3:30])=[CH:12][C:13]([CH3:29])([CH3:28])[NH:14]2.C(=O)([O-])[O-].[K+].[K+].[CH2:39](Br)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.C(OCC)(=O)C>CN(C)C=O>[CH2:39]([O:25][C:22]1[CH:23]=[CH:24][C:19]([C:18]2[C:9]([CH2:8][O:7][C:6]3[CH:31]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=3[CH3:32])=[C:10]3[C:15](=[CH:16][CH:17]=2)[NH:14][C:13]([CH3:28])([CH3:29])[CH:12]=[C:11]3[CH3:30])=[C:20]([O:26][CH3:27])[CH:21]=1)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

5-(5-Fluoro-2-methylphenoxymethyl)-6-(4-hydroxy-2-methoxyphenyl)-2,2,4-tri methyl-1,2-dihydroquinoline (Reference Compound No. 5-3, 20.1 mg, 0.046 mmol), potassium carbonate (16.7 mg, 0.12 mmol) and benzyl bromide (6.6 μL, 0.055 mmol) were dissolved in anhydrous N,N-dimethylformamide (0.5 mL), and the mixture was stirred at 60° C. for 40 minutes. Ethyl acetate (50 mL) was added to the reaction mixture, and the whole was washed with water (50 mL) and saturated brine (30 mL), dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give the titled compound (5.1 mg) as a colorless oil. (Yield 19%)

Aufarbeitung

washthe whole was washed with water (50 mL) and saturated brine (30 mL)
dry with materialdried over anhydrous magnesium sulfate
customthe solvent was removed under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag: ord-a4c1c49482b24fedb27af8b3e27d7dd1
Quelldatensatz: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08420635B2

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