Potassium Carbonate → 1h-Indazole,5-(2-fluoro-4-nitrophenoxy)-

HRID 16399

Reaktionsgleichung

[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[CH:5]2.[F:11][C:12]1[CH:13]=[C:14]([N+:19]([O-:21])=[O:20])[CH:15]=[CH:16][C:17]=1F.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[F:11][C:12]1[CH:13]=[C:14]([N+:19]([O-:21])=[O:20])[CH:15]=[CH:16][C:17]=1[O:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[CH:5]2

Komponenten

Reaktionsbedingungen

Temperatur: 40 °C

Versuchsvorschrift

5.00 g (37.3 mmol) of 5-hydroxyindazole are dissolved in 40 ml of anhydrous DMF. 5.93 g (37.3 mmol) of 3,4-difluoronitrobenzene and 5.15 g (37.3 mmol) of potassium carbonate are added, and the mixture is stirred at 40° C. overnight. For work-up, the mixture is filtered off with suction through kieselguhr, diluted with water and extracted three times with ethyl acetate. The combined organic phases are washed 1× with saturated aqueous sodium chloride solution, dried over sodium sulfate and concentrated using a rotary evaporator. The residue is chromatographed twice on silica gel using cyclohexane/ethyl acetate 3:1→1:1→1:2 and then purified by preparative HPLC.

Aufarbeitung

filtrationFor work-up, the mixture is filtered off with suction through kieselguhr
additiondiluted with water
extractionextracted three times with ethyl acetate
washThe combined organic phases are washed 1× with saturated aqueous sodium chloride solution
dry with materialdried over sodium sulfate
concentrationconcentrated
customa rotary evaporator
customThe residue is chromatographed twice on silica gel
custompurified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag: ord-148ed9b344d04550bc6dd240a54fb706
Quelldatensatz: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07737153B2

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