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Potassium Carbonate → 6-Fluoro-3-methoxy-[2,3']bipyridine

HRID 228805
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 228805
[F:1][C:2]1[N:7]=[C:6](I)[C:5]([O:9][CH3:10])=[CH:4][CH:3]=1.[N:11]1[CH:16]=[CH:15][CH:14]=[C:13](B(O)O)[CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[F:1][C:2]1[N:7]=[C:6]([C:13]2[CH:12]=[N:11][CH:16]=[CH:15][CH:14]=2)[C:5]([O:9][CH3:10])=[CH:4][CH:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 27343783-Pyridinylboronic acidHCID 23078267HCID 23078267, Verbindung

Produkt 1

HCID 688289086-Fluoro-3-methoxy-[2,3']bipyridineAusbeute 73,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

6-Fluoro-2-iodo-3-methoxypyridine (52 mg), tetrakistriphenylphosphine palladium(0) (24 mg), and 3-pyridineboronic acid (76 mg) were suspended in a mixed solvent composed of N,N-dimethylformamide (0.75 ml) and a 2 N aqueous potassium carbonate solution (0.75 ml), and the suspension was stirred at 80° C. for 4 hr. The reaction solution was cooled to room temperature, the reaction solution was then filtered, and the solvent was removed from the filtrate by distillation under the reduced pressure. Water was then added to the residue, and the mixture was extracted with dichloromethane. The dichloromethane layer was washed with water and saturated brine and was dried over anhydrous magnesium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography using acetone-chloroform to give 6-fluoro-3-methoxy-[2,3′]bipyridine (31 mg, yield 72%).

Aufarbeitung

  1. filtrationthe reaction solution was then filtered
  2. customthe solvent was removed from the filtrate by distillation under the reduced pressure
  3. additionWater was then added to the residue
  4. extractionthe mixture was extracted with dichloromethane
  5. washThe dichloromethane layer was washed with water and saturated brine
  6. dry with materialwas dried over anhydrous magnesium sulfate
  7. customThe solvent was removed by distillation under the reduced pressure
  8. customthe residue was purified by thin layer chromatography

Quellen und Nachweise

ORD-Eintrag
ord-530da0073a854aab8481e403c932f469
Quelldatensatz
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07560558B2

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