Reaction #91658

Reaction equation

2-Bromopyridin-3-ol

3-thiophenyl boronic acid

sodium carbonate

→

2-(thiophene-3-yl)pyridin-3-ol

Yield 48.6%

Solvents

dimethoxyethane water

Conditions

Workup

1. 1
   OtherAfter the completion of the reaction
2. 2
   Filtrationthe reaction mixture was filtered
3. 3
   workup.ADDITIONThe filtrate was added with water
4. 4
   Extractionextracted with ethyl acetate
5. 5
   DryingThe obtained organic layer was dried over magnesium sulfate
6. 6
   Otherpurified by column chromatography (ethyl acetate:hexane=1:3)

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%).

Source