Reacción #2254153

Ecuación de reacción

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

Rendimiento 61.0%

Disolventes

DMF

ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaAfter cooling
2. 2
   Filtraciónthe precipitated product was filtered off with suction
3. 3
   OtroThe organic phase of the filtrate was removed
4. 4
   Extracciónthe aqueous phase was extracted three times with ethyl acetate
5. 5
   SecadoThe combined organic phases were dried over magnesium sulphate
6. 6
   Otrothe solvent was removed under reduced pressure
7. 7
   workup.STIRRINGThe residue was stirred with dichloromethane
8. 8
   Filtraciónfiltered off with suction

Procedimiento

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.

Fuente