تفاعل #2254153

معادلة التفاعل

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

المردود 61.0%

المذيبات

DMF

ethyl acetate

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةAfter cooling
2. 2
   ترشيحthe precipitated product was filtered off with suction
3. 3
   أخرىThe organic phase of the filtrate was removed
4. 4
   استخلاصthe aqueous phase was extracted three times with ethyl acetate
5. 5
   تجفيفThe combined organic phases were dried over magnesium sulphate
6. 6
   أخرىthe solvent was removed under reduced pressure
7. 7
   workup.STIRRINGThe residue was stirred with dichloromethane
8. 8
   ترشيحfiltered off with suction

الإجراء التجريبي

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.

المصدر