Hydrochloric Acid → 5-Bromo-3-[3,5-diisopropyl-4-(2-morpholin-4-ylethoxy)-benzylidene]-1,3-dihydroindol-2-one

HRID 24410Notes

Reaction equation

HRID 24410 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([CH:21]([CH3:23])[CH3:22])[C:11]=1[O:12][CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)[CH:7]=O)([CH3:3])[CH3:2].[Br:24][C:25]1[CH:26]=[C:27]2[C:31](=[CH:32][CH:33]=1)[NH:30][C:29](=[O:34])[CH2:28]2.N1CCCC1.Cl>C(O)C>[Br:24][C:25]1[CH:26]=[C:27]2[C:31](=[CH:32][CH:33]=1)[NH:30][C:29](=[O:34])[C:28]2=[CH:7][C:6]1[CH:5]=[C:4]([CH:1]([CH3:3])[CH3:2])[C:11]([O:12][CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)=[C:10]([CH:21]([CH3:23])[CH3:22])[CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 31268PyrrolidineHCID 6111935-Bromo-2-oxindoleHCID 225711303,5-Diisopropyl-4-(2-morpholin-4-ylethoxy)-benzaldehyde

Product 1

HCID 545215295-Bromo-3-[3,5-diisopropyl-4-(2-morpholin-4-ylethoxy)-benzylidene]-1,3-dihydroindol-2-oneYield 13%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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.

Workup

  1. customthe solids removed by filtration
  2. washwashed with more water (50 ml)
  3. dissolutionThe solids were then dissolved in ethyl acetate (200 ml)
  4. washthe solution washed with 1N hydrochloric acid (75 ml) and brine (75 ml)
  5. dry with materialdried with magnesium sulfate
  6. concentrationconcentrated
  7. customThe crude solid was chromatographed (silica, 4:4:1 dichloromethane:hexanes:methanol)

Sources & evidence

ORD record
ord-852d5fa29554431f972a093846689cb0
Source dataset
uspto-grants-2005_02
Patent number
US06855730B2

Reaction notes

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