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Acetate → 4-(cyclopropylmethyl)-2-(4-fluoro-2-methylphenyl)pyrido[2,3-b]pyrazin-3(4H)-one

HRID 1924465
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1924465
Br[C:2]1[C:7](=[O:8])[N:6]([CH2:9][CH:10]2[CH2:12][CH2:11]2)[C:5]2[N:13]=[CH:14][CH:15]=[CH:16][C:4]=2[N:3]=1.[F:17][C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[C:20]([CH3:27])[CH:19]=1.C(=O)([O-])[O-].[Na+].[Na+].C([O-])(=O)C>CN(C)C=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.O.C(O)C>[CH:10]1([CH2:9][N:6]2[C:7](=[O:8])[C:2]([C:21]3[CH:22]=[CH:23][C:18]([F:17])=[CH:19][C:20]=3[CH3:27])=[N:3][C:4]3[CH:16]=[CH:15][CH:14]=[N:13][C:5]2=3)[CH2:12][CH2:11]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 175AcetateHCID 10340Sodium CarbonateHCID 2734665(4-Fluoro-2-methylphenyl)boronic acidHCID 581031982-bromo-4-(cyclopropylmethyl)pyrido[2,3-b]pyrazin-3(4H)-one

Produkt 1

HCID 442187314-(cyclopropylmethyl)-2-(4-fluoro-2-methylphenyl)pyrido[2,3-b]pyrazin-3(4H)-oneAusbeute 45,3 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 6102075Dichlorobis(triphenylphosphine)palladiumKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To 200 mg (0.71 mM) of 2-bromo-4-(cyclopropylmethyl)pyrido[2,3-b]pyrazin-3(4H)-one and 25.3 mg (0.036 mM) of bis(triphenylphosphine) palladium(II)chloride in 1 ml of dimethylformamide were added 142.9 mg (0.93 mM) of (4-fluoro-2-methylphenyl)boronic acid, 0.1 ml of ethanol and 715 μl of a 2M aqueous solution of sodium carbonate. The reaction mixture was then refluxed for 20 h under stirring. Water and ethyle acetate were added. The organic layer was separated, washed with water, dried on anhydrous sodium sulfate and the solvent was removed under vacuum. The compound was further purified by silica gel column chromatography, using dichloromethane as eluant, to give, after evaporation, 100 mg of 4-(cyclopropyl methyl)-2-(4-fluoro-2-methylphenyl)pyrido[2,3-b]pyrazin-3(4H)-one as a white solid. (Yield: 45.3%)

Aufarbeitung

  1. temperatureThe reaction mixture was then refluxed for 20 h
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materialdried on anhydrous sodium sulfate
  5. customthe solvent was removed under vacuum
  6. customThe compound was further purified by silica gel column chromatography
  7. customto give
  8. customafter evaporation, 100 mg of 4-(cyclopropyl methyl)-2-(4-fluoro-2-methylphenyl)pyrido[2,3-b]pyrazin-3(4H)-one as a white solid

Quellen und Nachweise

ORD-Eintrag
ord-2b1db21b166948fa860d7933e2b6cd35
Quelldatensatz
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08178556B2

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