5-Bromo-2-oxindole → 5-bromo-3-[3,5-dimethyl-4-(3-morpholin-4-yl-propyl)-1H-pyrrol-2-ylmethylene]-1,3-dihydroindol-2-one

HRID 1937617Notes

Reaction equation

HRID 1937617 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.[CH3:12][C:13]1[C:17]([CH2:18][CH2:19][CH2:20][N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)=[C:16]([CH3:27])[NH:15][C:14]=1[CH:28]=O>N1CCCC1.C(O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[CH:28][C:14]1[NH:15][C:16]([CH3:27])=[C:17]([CH2:18][CH2:19][CH2:20][N:21]2[CH2:22][CH2:23][O:24][CH2:25][CH2:26]2)[C:13]=1[CH3:12]

Participants

5

Reactant 2

HCID 6111935-Bromo-2-oxindoleHCID 219257263,5-dimethyl-4-(3-morpholin-4-yl-propyl)-1H-pyrrole-2-carbaldehyde

Product 1

HCID 543114565-bromo-3-[3,5-dimethyl-4-(3-morpholin-4-yl-propyl)-1H-pyrrol-2-ylmethylene]-1,3-dihydroindol-2-oneYield 90%

Reagents, catalysts & solvents 2

HCID 31268PyrrolidineCatalystHCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 5-bromo-1,3-dihydroindol-2-one (212 mg, 1.0 mmol), 3,5-dimethyl-4-(3-morpholin-4-yl-propyl)-1H-pyrrole-2-carbaldehyde (250 mg, 1.0 mmol) and 3 drops pyrrolidine in 2.0 ml of ethanol was refluxed at 90° C. for 4 hours and then cooled to room temperature. The precipitate was filtered, washed with cold ethanol and hexane and dried in a vacuum oven overnight to give 399.8 mg (90%) of 5-bromo-3-[3,5-dimethyl-4-(3-morpholin-4-yl-propyl)-1H-pyrrol-2-ylmethylene]-1,3-dihydroindol-2-one as a red solid:

Workup

  1. temperaturecooled to room temperature
  2. filtrationThe precipitate was filtered
  3. washwashed with cold ethanol and hexane
  4. customdried in a vacuum oven overnight

Sources & evidence

ORD record
ord-a92f4547e4084d518f37bce4c9aa5781
Source dataset
uspto-grants-2002_05
Patent number
US06395734B1

Reaction notes

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