反応 #2867

反応方程式

3-bromopyridine

2-Thiophene boronic acid

sodium carbonate

→

title compound

収率 16.3%

3-Thiophene-2-yl-pyridine

収率 16.3%

溶媒

dimethoxyethane

反応条件

後処理

1. 1
   温度the resulting mixture is refluxed overnight
2. 2
   温度The solution is cooled to room temperature
3. 3
   ろ過filtered through Celite
4. 4
   抽出The filtrated is extracted with ether (2×30 mL)
5. 5
   乾燥The combined organic layers are dried over MgSO4
6. 6
   ろ過filtered
7. 7
   濃縮concentrated
8. 8
   その他The crude product is purified by column chromatography
9. 9
   洗浄eluting with a gradient of 10% EtOAc/hexanes to 20% EtOAc/hexanes

実験手順

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.

出典