Réaction #52688

Équation de réaction

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

Rendement 13.0%

Solvants

ethanol

Conditions de réaction

Traitement

1. 1
   Autrethe solids removed by filtration
2. 2
   Lavagewashed with more water (50 ml)
3. 3
   workup.DISSOLUTIONThe solids were then dissolved in ethyl acetate (200 ml)
4. 4
   Lavagethe solution washed with 1N hydrochloric acid (75 ml) and brine (75 ml)
5. 5
   Séchagedried with magnesium sulfate
6. 6
   Concentrationconcentrated
7. 7
   AutreThe crude solid was chromatographed (silica, 4:4:1 dichloromethane:hexanes:methanol)

Mode opératoire

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.

Source