تفاعل #2867

معادلة التفاعل

3-bromopyridine

2-Thiophene boronic acid

sodium carbonate

→

title compound

المردود 16.3%

3-Thiophene-2-yl-pyridine

المردود 16.3%

المذيبات

dimethoxyethane

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthe resulting mixture is refluxed overnight
2. 2
   درجة الحرارةThe solution is cooled to room temperature
3. 3
   ترشيحfiltered through Celite
4. 4
   استخلاصThe filtrated is extracted with ether (2×30 mL)
5. 5
   تجفيفThe combined organic layers are dried over MgSO4
6. 6
   ترشيحfiltered
7. 7
   تركيزconcentrated
8. 8
   أخرىThe crude product is purified by column chromatography
9. 9
   غسيلeluting with a gradient of 10% EtOAc/hexanes to 20% EtOAc/hexanes

الإجراء التجريبي

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.

المصدر