Bromoacetate → ethyl 3-[3-(4-fluorophenyl)-1H-pyrazolo[3,4-b]pyridin-1-yl]phenoxyacetate
Reaktionsgleichung
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[N:10]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([OH:23])[CH:18]=3)[N:9]=2)=[CH:4][CH:3]=1.Br[CH2:25][C:26]([O-])=O.[C:29](=[O:32])([O-])[O-:30].[K+].[K+].[CH3:35]N(C)C=O>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[N:10]([C:17]3[CH:18]=[C:19]([CH:20]=[CH:21][CH:22]=3)[O:23][CH2:35][C:29]([O:30][CH2:25][CH3:26])=[O:32])[N:9]=2)=[CH:4][CH:3]=1Komponenten
5
Reaktionsbedingungen
- Temperatur
- 65 °C
Versuchsvorschrift
In 200 ml of dimethylformamide were suspended 20 g of 3-(4-fluorophenyl)-1-(3-hydroxyphenyl)-1H-pyrazolo[3,4-b]pyridine, 21.9 g of bromoacetate and 18.1 g of potassium carbonate. The mixture was stirred at 65° C. for 4 hours. The reaction mixture was concentrated under reduced pressure. The residue was extracted with ethyl acetate-water. The organic layer was concentrated. Hexane was added to the residue for crystallization. The obtained crude crystals were recrystallized from isopropyl ether to give 10.9 g of ethyl 3-[3-(4-fluorophenyl)-1H-pyrazolo[3,4-b]pyridin-1-yl]phenoxyacetate, m.p. 130°-131° C.
Aufarbeitung
- concentrationThe reaction mixture was concentrated under reduced pressure
- extractionThe residue was extracted with ethyl acetate-water
- concentrationThe organic layer was concentrated
- additionHexane was added to the residue for crystallization
- customThe obtained crude crystals
- customwere recrystallized from isopropyl ether
Quellen und Nachweise
- ORD-Eintrag
- ord-9164fce7ed04476483c591b2ab31585e
- Quelldatensatz
- uspto-grants-1991_04
- Patentnummer
- US05006520
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