Dimethylformamide → [8-chloro-3-(4-chlorophenylsulfanyl)-4-difluoromethoxy-2-methylquinolin-5-yloxy]acetic Acid Methyl Ester

HRID 2266473Notizen

Reaktionsgleichung

[CH3:1][O:2][C:3](=[O:27])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]2[C:7]=1[C:8](=[O:26])[C:9]([S:18][C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1)=[C:10]([CH3:17])[NH:11]2.CN(C)C=O.C(=O)([O-])[O-].[K+].[K+].Cl[C:40](OC(=O)C)([F:42])[F:41]>O>[CH3:1][O:2][C:3](=[O:27])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]2[C:7]=1[C:8]([O:26][CH:40]([F:42])[F:41])=[C:9]([S:18][C:19]1[CH:20]=[CH:21][C:22]([Cl:25])=[CH:23][CH:24]=1)[C:10]([CH3:17])=[N:11]2

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

A mixture of [8-chloro-3-(4-chlorophenylsulfanyl)-2-methyl-4-oxo-1,4-dihydroquinolin-5-yloxy]acetic acid methyl ester (0.26 g), N,N-dimethylformamide (5.0 mL), potassium carbonate (0.25 g) and acetic acid chlorodifluoromethyl ester (0.13 mL) was stirred at 80° C. for 17 hour. The mixture was diluted with water and extracted with ethyl acetate. The combined extracts were washed with saturated aqueous sodium chloride solution and dried over magnesium sulfate. The solvent was removed under reduced pressure and the residue purified by column chromatography on silica gel, eluting with a mixture of dichloromethane and cyclohexane (7:3 by volume) to afford title compound, 0.044 g.

Aufarbeitung

extractionextracted with ethyl acetate
washThe combined extracts were washed with saturated aqueous sodium chloride solution
dry with materialdried over magnesium sulfate
customThe solvent was removed under reduced pressure
customthe residue purified by column chromatography on silica gel
washeluting with a mixture of dichloromethane and cyclohexane (7:3 by volume)

Quellen und Nachweise

ORD-Eintrag: ord-5474c21921724986963c0cbf913c0e6d
Quelldatensatz: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07858640B2

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