Bromoacetate → HCID 14796397, Verbindung

HRID 1084846

Reaktionsgleichung

Reaktionsgleichung von HRID 1084846
[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]=1

Komponenten

5

Edukt 4

HCID 6226BromoacetateHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 147962583-(4-fluorophenyl)-1-(3-hydroxyphenyl)-1H-pyrazolo[3,4-b]pyridine

Produkt 1

HCID 14796397HCID 14796397, Verbindung

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

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionThe residue was extracted with ethyl acetate-water
  3. concentrationThe organic layer was concentrated
  4. additionHexane was added to the residue for crystallization
  5. customThe obtained crude crystals
  6. customwere recrystallized from isopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-9164fce7ed04476483c591b2ab31585e
Quelldatensatz
uspto-grants-1991_04
Patentnummer
US05006520

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