Cesium carbonate → HCID 19805500, Verbindung

HRID 1681697

Reaktionsgleichung

Cl[CH2:2][C:3]1[N:4]([CH3:8])[CH:5]=[CH:6][N:7]=1.[C:9]([N:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16](=[O:23])[NH:15]1)([O:11][CH2:12][CH3:13])=[O:10].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[C:9]([N:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16](=[O:23])[N:15]1[CH2:2][C:3]1[N:4]([CH3:8])[CH:5]=[CH:6][N:7]=1)([O:11][CH2:12][CH3:13])=[O:10]

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

2-Chloromethyl-1-methylimidazole (0.91 g) was added portionwise to a stirred mixture of 1,2-dihydro-1-carboethoxy-3H-indazol-3-one (1.03 g), caesium carbonate (5.4 g) and N,N-dimethylformamide (DMF, 5 ml). The mixture was heated to 80° C. for 4 hours under an atmosphere of argon, cooled to ambient temperature and filtered. The filtrate was diluted with water and extracted with ethyl acetate. The solid was washed with ethyl acetate. The organic solutions were combined, washed with a saturated aqueous sodium chloride solution, dried (MgSO4) and evaporated. The oil residue crystallised on trituration under diethyl ether. There was thus obtained a mixture (1 g, 67% of 1,2-dihydro-1-carboethoxy-2-(1-methylimidazol-2-yl)methyl-3H-indazol-3-one and 1-carboethoxy-3-(1-methylimidazol-2-yl)methoxy-1H-indazole (starting material for Ex. 145).

Aufarbeitung

temperaturecooled to ambient temperature
filtrationfiltered
additionThe filtrate was diluted with water
extractionextracted with ethyl acetate
washThe solid was washed with ethyl acetate
washwashed with a saturated aqueous sodium chloride solution
dry with materialdried (MgSO4)
customevaporated
customThe oil residue crystallised on trituration under diethyl ether

Quellen und Nachweise

ORD-Eintrag: ord-88a00675ace7406b80429698b46d43a3
Quelldatensatz: uspto-grants-1992_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05173496

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