Potassium Carbonate → N,N-diethyl-3-[3-(4-fluorophenyl)-1H-pyrazolo[3,4-b]pyridin-1yl]phenoxyacetamide

HRID 1084837

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

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

In 75 ml of dimethylformamide were suspended 5.0 g of 3-(4-fluorophenyl)-1-(3-hydroxyphenyl)-1H-pyrazolo[3,4-b]pyridine, 3.5 g of N,N-diethylbromoacetamide and 2.5 g of potassium carbonate. The mixture was stirred at 60° C. for 5 hours. After the solvent was distilled off under reduced pressure, the residue was extracted with ethyl acetate-water. The organic layer was concentrated. Isopropyl ether was added to the residue for crystallization. The obtained crude crystals were recrystallized from ethyl acetate to give 2.8 g of N,N-diethyl-3-[3-(4-fluorophenyl)-1H-pyrazolo[3,4-b]pyridin-1yl]phenoxyacetamide, m.p. 102°-105° C.

Aufarbeitung

distillationAfter the solvent was distilled off under reduced pressure
extractionthe residue was extracted with ethyl acetate-water
concentrationThe organic layer was concentrated
additionIsopropyl ether was added to the residue for crystallization
customThe obtained crude crystals
customwere recrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag: ord-2d06a56142c04d5bbfddb29f84459f6c
Quelldatensatz: uspto-grants-1991_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05006520

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