تفاعل #2200598

معادلة التفاعل

methylboronic acid

cesium fluoride

1,4-bis(diphenylphosphino)butane

methyl 4-amino-3,6-dichloro-5-fluoropyridine-2-carboxylate

→

methyl 4-amino-3-chloro-5-fluoro-6-methylpyridine-2-carboxylate

المذيبات

acetonitrile

triethylamine

water

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthe reaction mixture heated
2. 2
   درجة الحرارةunder reflux overnight
3. 3
   درجة الحرارةAfter cooling
4. 4
   استخلاصthe mixture extracted with ethyl acetate
5. 5
   غسيلThe organic layer was washed with brine
6. 6
   تجفيفdried (MgSO4)
7. 7
   تركيزconcentrated
8. 8
   أخرىThe residue was purified by column chromatography (33% ethyl acetate in hexane)

الإجراء التجريبي

A solution of methylboronic acid (0.17 g, 2.93 mmol), cesium fluoride (0.95 g, 6.27 mmol), 1,4-bis(diphenylphosphino)butane (0.09 g, 0.21 mmol), methyl 4-amino-3,6-dichloro-5-fluoropyridine-2-carboxylate (0.50 g, 2.09 mmol) and triethylamine (1 mL) in acetonitrile (20 mL) was purged for 15 minutes with nitrogen. Palladium acetate (0.05 g, 0.21 mmol) was then added and the reaction mixture heated under reflux overnight. After cooling, water was added and the mixture extracted with ethyl acetate. The organic layer was washed with brine, dried (MgSO4), and concentrated. The residue was purified by column chromatography (33% ethyl acetate in hexane) to give methyl 4-amino-3-chloro-5-fluoro-6-methylpyridine-2-carboxylate (0.23 g, 1.05 mmol), mp 113-114° C.

المصدر