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Potassium Carbonate → 6-(4-Methoxyphenyl)-2-pyridinecarbonitrile

HRID 499458
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 499458
Cl[C:2]1[N:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][CH:3]=1.[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15](OB(O)O)=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C(O)C.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.O.C(OCC)(=O)C>[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:2]2[N:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][CH:3]=2)=[CH:14][CH:13]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 3

HCID 11430Potassium CarbonateHCID 1184246-Chloropyridine-2-carbonitrileHCID 147699944-Methoxyphenyl boric acid

Produkt 1

HCID 229396246-(4-Methoxyphenyl)-2-pyridinecarbonitrileAusbeute 89,4 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 178418397HCID 178418397, Verbindung
Katalysator
HCID 702EthanolLösungsmittel
HCID 962WaterLösungsmittel2×
HCID 1140TolueneLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

6-Chloro-2-pyridinecarbonitrile (0.70 g, 5.0 mmol) and 4-methoxyphenylboric acid (1.17 g, 7.7 mmol) were dissolved in toluene (60 ml)-ethanol (15 ml), and potassium carbonate (1.75 g, 12.6 mmol) and water (15 ml) were added thereto. The mixture was deairated under reduced pressure for 10 minutes. Tetrakis(triphenylphosphine)palladium (0) (0.29 g, 0.25 mmol) was added to the reaction mixture under argon atmosphere, and the mixture was refluxed for 16 hrs. The reaction mixture was combined with ethyl acetate and water. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was subjected to a silica gel column chromatography. The fractions eluted with hexane-ethyl acetate (4:1, v/v) were collected, concentrated and recrystallized from hexane-ethyl acetate to give the titled compound (0.94 g, 88%).

Aufarbeitung

  1. additionwere added
  2. temperaturethe mixture was refluxed for 16 hrs
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated
  6. washThe fractions eluted with hexane-ethyl acetate (4:1
  7. customv/v) were collected
  8. concentrationconcentrated
  9. customrecrystallized from hexane-ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-0645fc9362f64f5db395b680ed297e74
Quelldatensatz
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07767665B2

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