Potassium Carbonate → 1-[1-[1-(4-Fluorophenyl)-5-isopropyl-pyrazol-4-yl]-2-oxo-pyrrolidin-3-yl]pyrazolo[3,4-b]pyridine-3-carbonitrile

HRID 522320Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 522320
Br[CH:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:8]=[N:9][N:10]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[C:11]=2[CH:12]([CH3:14])[CH3:13])[C:3]1=[O:22].[NH:23]1[C:27]2=[N:28][CH:29]=[CH:30][CH:31]=[C:26]2[C:25]([C:32]#[N:33])=[N:24]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[F:21][C:18]1[CH:19]=[CH:20][C:15]([N:10]2[C:11]([CH:12]([CH3:14])[CH3:13])=[C:7]([N:4]3[CH2:5][CH2:6][CH:2]([N:23]4[C:27]5=[N:28][CH:29]=[CH:30][CH:31]=[C:26]5[C:25]([C:32]#[N:33])=[N:24]4)[C:3]3=[O:22])[CH:8]=[N:9]2)=[CH:16][CH:17]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 867230343-Bromo-1-[1-(4-fluorophenyl)-5-isopropylpyrazol-4-yl]pyrrolidin-2-oneHCID 178510690HCID 178510690, Verbindung

Produkt 1

HCID 867230351-[1-[1-(4-Fluorophenyl)-5-isopropyl-pyrazol-4-yl]-2-oxo-pyrrolidin-3-yl]pyrazolo[3,4-b]pyridine-3-carbonitrileAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of 3-bromo-1-[1-(4-fluorophenyl)-5-isopropylpyrazol-4-yl]pyrrolidin-2-one (0.080 g, 0.22 mmol), 1H-pyrazolo[3,4-b]pyridine-3-carbonitrile (0.045 g, 0.31 mmol) and K2CO3 (0.070 g, 0.50 mmol) in DMF (2.5 mL) was stirred at 60° C. for 1 hr. It was then cooled to room temperature, quenched with water (30 mL) and extracted with EtOAc (100 mL). The organic layer was separated, dried over anhydrous sodium sulfate, concentrated in vacuo and purified by flash chromatography (SiO2, 0˜100% EtOAc/hexanes gradient elution) to give 1-[1-[1-(4-fluorophenyl)-5-isopropyl-pyrazol-4-yl]-2-oxo-pyrrolidin-3-yl]pyrazolo[3,4-b]pyridine-3-carbonitrile (0.085 g, 88%).

Aufarbeitung

  1. temperatureIt was then cooled to room temperature
  2. customquenched with water (30 mL)
  3. extractionextracted with EtOAc (100 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. custompurified by flash chromatography (SiO2, 0˜100% EtOAc/hexanes gradient elution)

Quellen und Nachweise

ORD-Eintrag
ord-6d91d2b9b2734b548a76f83bd4dc0eba
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09328116B2

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