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

HRID 63378

Reaction equation

HRID 63378 reaction equation
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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 18180031Water 1,2-dimethoxyethaneSolvent

Conditions

Temperature
120 °C

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-753d541b0a1a4293a8ab763930e70e3e
Source dataset
uspto-grants-2016_09
Patent number
US09447083B2

Linked notes

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