Réaction #2867

Équation de réaction

3-bromopyridine

2-Thiophene boronic acid

sodium carbonate

→

title compound

Rendement 16.3%

3-Thiophene-2-yl-pyridine

Rendement 16.3%

Solvants

dimethoxyethane

Conditions de réaction

Traitement

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

Mode opératoire

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