Diphenyl Ether → (4-hydroxy-1-phenyl-1H-pyrazolo[3,4-b]pyridin-5-yl)(phenyl)methanone

HRID 563444

Reaktionsgleichung

Reaktionsgleichung von HRID 563444
[C:1]([C:9](=[CH:15]OCC)[C:10]([O:12]CC)=O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19]1([N:25]2[C:29]([NH2:30])=[CH:28][CH:27]=[N:26]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C1(OC2C=CC=CC=2)C=CC=CC=1>C(OCC)(=O)C>[OH:12][C:10]1[C:9]([C:1]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:8])=[CH:15][N:30]=[C:29]2[N:25]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:26]=[CH:27][C:28]=12

Komponenten

5

Edukt 3

HCID 7583Diphenyl EtherHCID 700061-Phenylpyrazol-5-ylamineHCID 98006Ethyl 2-benzoyl-3-ethoxyacrylate

Produkt 1

HCID 178519487(4-hydroxy-1-phenyl-1H-pyrazolo[3,4-b]pyridin-5-yl)(phenyl)methanoneAusbeute 42,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of ethyl 2-benzoyl-3-ethoxyacrylate (0.99 g, 4.0 mmol) and 1-phenyl-1H-pyrazol-5-amine (0.64 g, 4.0 mmol) was stirred at 120° C. for 1.5 hr under argon and then cooled. After diphenyl ether (5 g) was added, the mixture was stirred at 240° C. for 2 hr under argon. Flash chromatography and crystallization in heptane and ethyl acetate mixture gave (4-hydroxy-1-phenyl-1H-pyrazolo[3,4-b]pyridin-5-yl)(phenyl)methanone (0.53 g, 1.7 mmol, 42% yield) as a yellow solid.

Aufarbeitung

  1. temperaturecooled
  2. stirringthe mixture was stirred at 240° C. for 2 hr under argon
  3. customFlash chromatography and crystallization in heptane

Quellen und Nachweise

ORD-Eintrag
ord-0d50ff87a0124408aa0b2972be4ee475
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08067447B2

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