Sodium Carbonate → 3-Hydroxy-2-(3-furyl)pyridine

HRID 63378

Reaktionsgleichung

Reaktionsgleichung von HRID 63378
Br[C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[O:9]1[CH:13]=[CH:12][C:11](B(O)O)=[CH:10]1.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.O>[O:9]1[CH:13]=[CH:12][C:11]([C:2]2[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=2)=[CH:10]1

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 230702-Bromo-3-pyridinolHCID 2734358Furan-3-boronic acid

Produkt 1

HCID 831299213-Hydroxy-2-(3-furyl)pyridineAusbeute 27 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 18180031Water 1,2-dimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

2-Bromopyridin-3-ol (200 mg, 1.15 mmol), 3-furan boronic acid (574 mg, 1.38 mmol), sodium carbonate (365 mg, 12.8 mmol) and Pd2(dppf)2Cl2 (187 mg, 0.23 mmol) were dissolved in dimethoxyethane/water 2 mL/1 mL, followed by stirring in microwave at 120° C. for 20 minutes. After the completion of the reaction, the reaction mixture was filtered using Celite. The filtrate was added with water, and extracted with ethyl acetate. The obtained organic layer was dried over magnesium sulfate, and purified by column chromatography (ethyl acetate:hexane=1:3) to obtain 2-(furan-3-yl)pyridin-3-ol (50 mg, 27%).

Aufarbeitung

  1. customAfter the completion of the reaction
  2. filtrationthe reaction mixture was filtered
  3. additionThe filtrate was added with water
  4. extractionextracted with ethyl acetate
  5. dry with materialThe obtained organic layer was dried over magnesium sulfate
  6. custompurified by column chromatography (ethyl acetate:hexane=1:3)

Quellen und Nachweise

ORD-Eintrag
ord-753d541b0a1a4293a8ab763930e70e3e
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447083B2

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