Reacción #2867

Ecuación de reacción

3-bromopyridine

2-Thiophene boronic acid

sodium carbonate

→

title compound

Rendimiento 16.3%

3-Thiophene-2-yl-pyridine

Rendimiento 16.3%

Disolventes

dimethoxyethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe resulting mixture is refluxed overnight
2. 2
   TemperaturaThe solution is cooled to room temperature
3. 3
   Filtraciónfiltered through Celite
4. 4
   ExtracciónThe filtrated is extracted with ether (2×30 mL)
5. 5
   SecadoThe combined organic layers are dried over MgSO4
6. 6
   Filtraciónfiltered
7. 7
   Concentraciónconcentrated
8. 8
   OtroThe crude product is purified by column chromatography
9. 9
   Lavadoeluting with a gradient of 10% EtOAc/hexanes to 20% EtOAc/hexanes

Procedimiento

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.

Fuente