반응 #2254153

반응 방정식

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

수율 61.0%

용매

DMF

ethyl acetate

반응 조건

후처리

1. 1
   온도After cooling
2. 2
   여과the precipitated product was filtered off with suction
3. 3
   기타The organic phase of the filtrate was removed
4. 4
   추출the aqueous phase was extracted three times with ethyl acetate
5. 5
   건조The combined organic phases were dried over magnesium sulphate
6. 6
   기타the solvent was removed under reduced pressure
7. 7
   workup.STIRRINGThe residue was stirred with dichloromethane
8. 8
   여과filtered off with suction

실험 절차

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.

출처