Reaction #2867

Reaction equation

3-bromopyridine

2-Thiophene boronic acid

sodium carbonate

→

title compound

Yield 16.3%

3-Thiophene-2-yl-pyridine

Yield 16.3%

Solvents

dimethoxyethane

Conditions

Workup

1. 1
   Temperaturethe resulting mixture is refluxed overnight
2. 2
   TemperatureThe solution is cooled to room temperature
3. 3
   Filtrationfiltered through Celite
4. 4
   ExtractionThe filtrated is extracted with ether (2×30 mL)
5. 5
   DryingThe combined organic layers are dried over MgSO4
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated
8. 8
   OtherThe crude product is purified by column chromatography
9. 9
   Washeluting with a gradient of 10% EtOAc/hexanes to 20% EtOAc/hexanes

Procedure

A mixture of 3-bromopyridine (1.30 mL, 13.5 mmol) and tetrakis(triphenylphosphine) (0.468 g, 0.41 mmol) in 40 mL of dimethoxyethane is stirred under nitrogen at room temperature for 10 min. 2-Thiophene boronic acid (1.90 g, 14.8 mmol) and 20 mL of 1N sodium carbonate are added and the resulting mixture is refluxed overnight. The solution is cooled to room temperature and filtered through Celite. The filtrated is extracted with ether (2×30 mL). The combined organic layers are dried over MgSO4, filtered and concentrated. The crude product is purified by column chromatography eluting with a gradient of 10% EtOAc/hexanes to 20% EtOAc/hexanes to afford the title compound (0.355 g, 2.20 mmol) as a light yellow oil.

Source