反応 #2254153

反応方程式

3-fluoro-5-(1,3-thiazol-2-yl)pyridine

6-bromopyridin-2-carbonitrile

water

tris(2-methylphenyl)phosphine

→

6-[2-(5-fluoropyridin-3-yl)-1,3-thiazol-5-yl]pyridine-2-carbonitrile

収率 61.0%

溶媒

DMF

ethyl acetate

反応条件

後処理

1. 1
   温度After cooling
2. 2
   ろ過the precipitated product was filtered off with suction
3. 3
   その他The organic phase of the filtrate was removed
4. 4
   抽出the aqueous phase was extracted three times with ethyl acetate
5. 5
   乾燥The combined organic phases were dried over magnesium sulphate
6. 6
   その他the solvent was removed under reduced pressure
7. 7
   workup.STIRRINGThe residue was stirred with dichloromethane
8. 8
   ろ過filtered off with suction

実験手順

Under argon, 3-fluoro-5-(1,3-thiazol-2-yl)pyridine (0.99 g, 5.47 mmol) and 6-bromopyridin-2-carbonitrile (1.0 g, 5.47 mmol) were initially charged in DMF (15 ml). After 10 min, at room temperature, tris(2-methylphenyl)phosphine (0.13 g, 0.23 mmol) and palladium(II) chloride (0.1 g, 0.55 mmol) were added. The reaction mixture was stirred at 130° C. for 14 h. After cooling, water and ethyl acetate were added and the precipitated product was filtered off with suction. The organic phase of the filtrate was removed and the aqueous phase was extracted three times with ethyl acetate. The combined organic phases were dried over magnesium sulphate and the solvent was removed under reduced pressure. The residue was stirred with dichloromethane and filtered off with suction. This gave a total of 0.94 g (61% of theory) of 6-[2-(5-fluoropyridin-3-yl)-1,3-thiazol-5-yl]pyridine-2-carbonitrile.

出典