反应 #52688

反应方程式

hydrochloric acid

3,5-diisopropyl-4-(2-morpholin-4-ylethoxy)-benzaldehyde

5-bromo-2-oxindole

pyrrolidine

→

5-bromo-3-[3,5-diisopropyl-4-(2-morpholin-4-ylethoxy)-benzylidene]-1,3-dihydroindol-2-one

收率 13.0%

溶剂

ethanol

反应条件

后处理

1. 1
   其他the solids removed by filtration
2. 2
   洗涤washed with more water (50 ml)
3. 3
   workup.DISSOLUTIONThe solids were then dissolved in ethyl acetate (200 ml)
4. 4
   洗涤the solution washed with 1N hydrochloric acid (75 ml) and brine (75 ml)
5. 5
   干燥dried with magnesium sulfate
6. 6
   浓缩concentrated
7. 7
   其他The crude solid was chromatographed (silica, 4:4:1 dichloromethane:hexanes:methanol)

实验过程

A mixture of 3,5-diisopropyl-4-(2-morpholin-4-ylethoxy)-benzaldehyde (0.4 g), 5-bromo-2-oxindole (0.27 g) and pyrrolidine (0.5 ml) in ethanol (2 ml) was held in a sealed tube at 100° C. for 12 hours. The mixture was then added to 1N hydrochloric acid (100 ml) and the solids removed by filtration and washed with more water (50 ml). The solids were then dissolved in ethyl acetate (200 ml), the solution washed with 1N hydrochloric acid (75 ml) and brine (75 ml), dried with magnesium sulfate and concentrated. The crude solid was chromatographed (silica, 4:4:1 dichloromethane:hexanes:methanol) to give 80 mg (13%) of 5-bromo-3-[3,5-diisopropyl-4-(2-morpholin-4-ylethoxy)-benzylidene]-1,3-dihydroindol-2-one as a reddish-brown solid.

来源