反应 #2200598

反应方程式

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

溶剂

acetonitrile

triethylamine

water

反应条件

后处理

1. 1
   温度the reaction mixture heated
2. 2
   温度under reflux overnight
3. 3
   温度After cooling
4. 4
   萃取the mixture extracted with ethyl acetate
5. 5
   洗涤The organic layer was washed with brine
6. 6
   干燥dried (MgSO4)
7. 7
   浓缩concentrated
8. 8
   其他The residue was purified by column chromatography (33% ethyl acetate in hexane)

实验过程

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.

来源