反応 #2290045

反応方程式

NaH

2,4-Difluorobenzyl bromide

1-(2-cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)-4-hydroxypyridin-2 (1H)-one

→

title compound

収率 35.0%

1-(2-Cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)-4-((2,4-difluorobenzyl)oxy)pyridin-2(1H)-one

収率 35.0%

溶媒

THF

THF

THF

反応条件

後処理

1. 1
   workup.STIRRINGthe resulting mixture was stirred at room temperature for further 3 h
2. 2
   温度by heating
3. 3
   温度at reflux for 6 h
4. 4
   温度The reaction mixture was then cooled to room temperature
5. 5
   その他quenched with ice-water
6. 6
   抽出The mixture was extracted with DCM
7. 7
   洗浄the extract was washed with brine
8. 8
   乾燥dried over Na2SO4
9. 9
   濃縮concentrated in vacuo
10. 10
    その他The crude product was purified by silica gel column chromatography (MeOH/DCM)

実験手順

To a stirred suspension of NaH (40% oil dispersion, 19 mg) in THF (6 ml) was added a solution of 1-(2-cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)-4-hydroxypyridin-2 (1H)-one (75 mg) in THF (1 ml) at 0° C., and then the mixture was stirred at room temperature for 30 min. 2,4-Difluorobenzyl bromide (67 mg) in THF (0.5 ml) was added, and the resulting mixture was stirred at room temperature for further 3 h followed by heating at reflux for 6 h. The reaction mixture was then cooled to room temperature and quenched with ice-water. The mixture was extracted with DCM, and the extract was washed with brine, dried over Na2SO4 and concentrated in vacuo. The crude product was purified by silica gel column chromatography (MeOH/DCM) to give the title compound (38 mg) as an off-white solid.

出典