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Water → 1-(4-Fluorophenyl)-5,6-dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile

HRID 2095858
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2095858
Br[C:2]1[CH:3]=[C:4]([C:17]#[N:18])[C:5](=[O:16])[N:6]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)[C:7]=1[CH3:8].[CH3:19][Sn](C)(C)C.O.C(OCC)(=O)C>CN(C)C=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:15][C:12]1[CH:13]=[CH:14][C:9]([N:6]2[C:7]([CH3:8])=[C:2]([CH3:19])[CH:3]=[C:4]([C:17]#[N:18])[C:5]2=[O:16])=[CH:10][CH:11]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 11661TetramethyltinHCID 581585675-Bromo-1-(4-fluorophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile

Produkt 1

HCID 581586481-(4-Fluorophenyl)-5,6-dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrileAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysator
HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a solution of 5-bromo-1-(4-fluorophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile (200 mg, 0.651 mmol) in N,N-dimethylformamide (2 mL) were added tetramethyltin (582 mg, 3.255 mmol) and tetrakistriphenylphosphinepalladium(0) (22.3 mg, 0.019 mmol), and the mixture was stirred at 120° C. for 17 hr. Water and ethyl acetate were added to the reaction mixture, and the mixture was extracted 3 times with ethyl acetate. The organic layer was washed with saturated brine, and the solvent was evaporated under reduced pressure. The obtained residue was washed with diethyl ether and collected by filtration to give the title compound (94 mg, 60%) as a white solid.

Aufarbeitung

  1. extractionthe mixture was extracted 3 times with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. customthe solvent was evaporated under reduced pressure
  4. washThe obtained residue was washed with diethyl ether
  5. filtrationcollected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-2f9a0660bb1b45d19042a08ba5b64311
Quelldatensatz
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08445509B2

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