Реакция #2867

Уравнение реакции

3-bromopyridine

2-Thiophene boronic acid

sodium carbonate

→

title compound

Выход 16.3%

3-Thiophene-2-yl-pyridine

Выход 16.3%

Растворители

dimethoxyethane

Условия реакции

Обработка

1. 1
   Температураthe resulting mixture is refluxed overnight
2. 2
   ТемператураThe solution is cooled to room temperature
3. 3
   Фильтрацияfiltered through Celite
4. 4
   ЭкстракцияThe filtrated is extracted with ether (2×30 mL)
5. 5
   СушкаThe combined organic layers are dried over MgSO4
6. 6
   Фильтрацияfiltered
7. 7
   Концентрированиеconcentrated
8. 8
   ДругоеThe crude product is purified by column chromatography
9. 9
   Промывкаeluting with a gradient of 10% EtOAc/hexanes to 20% EtOAc/hexanes

Методика

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.

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