반응 #2867

반응 방정식

3-bromopyridine

2-Thiophene boronic acid

sodium carbonate

→

title compound

수율 16.3%

3-Thiophene-2-yl-pyridine

수율 16.3%

용매

dimethoxyethane

반응 조건

후처리

1. 1
   온도the resulting mixture is refluxed overnight
2. 2
   온도The solution is cooled to room temperature
3. 3
   여과filtered through Celite
4. 4
   추출The filtrated is extracted with ether (2×30 mL)
5. 5
   건조The combined organic layers are dried over MgSO4
6. 6
   여과filtered
7. 7
   농축concentrated
8. 8
   기타The crude product is purified by column chromatography
9. 9
   세척eluting with a gradient of 10% EtOAc/hexanes to 20% EtOAc/hexanes

실험 절차

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.

출처