Reaktion #2867

Reaktionsgleichung

3-bromopyridine

2-Thiophene boronic acid

sodium carbonate

→

title compound

Ausbeute 16.3%

3-Thiophene-2-yl-pyridine

Ausbeute 16.3%

Lösungsmittel

dimethoxyethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe resulting mixture is refluxed overnight
2. 2
   TemperaturThe solution is cooled to room temperature
3. 3
   Filtrationfiltered through Celite
4. 4
   ExtraktionThe filtrated is extracted with ether (2×30 mL)
5. 5
   TrocknenThe combined organic layers are dried over MgSO4
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated
8. 8
   SonstigeThe crude product is purified by column chromatography
9. 9
   Wascheneluting with a gradient of 10% EtOAc/hexanes to 20% EtOAc/hexanes

Vorschrift

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.

Quelle