Sodium Carbonate → 3-Hydroxy-2-(thiophen-3-YL)pyridine

HRID 63380

Reaction equation

HRID 63380 reaction equation
Br[C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[S:9]1[CH:13]=[CH:12][C:11](B(O)O)=[CH:10]1.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.O>[S: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 581760Thiophene-3-boronic acid

Product 1

HCID 532174763-Hydroxy-2-(thiophen-3-YL)pyridineYield 48.6%

Reagents, catalysts & solvents 1

HCID 18180031Water 1,2-dimethoxyethaneSolvent

Conditions

Temperature
120 °C

Procedure

2-Bromopyridin-3-ol (100 mg, 0.58 mmol), 3-thiophenyl boronic acid (88 mg, 0.69 mmol), sodium carbonate (184 mg, 2.07 mmol) and Pd2(dppf)2Cl2 (94 mg, 0.12 mmol) were dissolved in dimethoxyethane/water of 1 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-(thiophene-3-yl)pyridin-3-ol (50 mg, 48%).

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-0ca8794b5619488e887182cf5776361d
Source dataset
uspto-grants-2016_09
Patent number
US09447083B2

Linked notes

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