3-(5-formyl-2,4-dimethyl-1H-pyrrol-3-yl)propanoic Acid → 3-(5-[6-(3-Ethoxy-phenyl)-2-oxo-1,2-dihydroindol-3-ylidenemethyl]-2,4-dimethyl-1H-pyrrol-3-yl)-propionic acid

HRID 1815412Notes

Reaction equation

HRID 1815412 reaction equation
[C:1]([CH2:4][CH2:5][C:6]1[C:10]([CH3:11])=[C:9]([CH:12]=O)[NH:8][C:7]=1[CH3:14])([OH:3])=[O:2].[CH2:15]([O:17][C:18]1[CH:19]=[C:20]([C:24]2[CH:32]=[C:31]3[C:27]([CH2:28][C:29](=[O:33])[NH:30]3)=[CH:26][CH:25]=2)[CH:21]=[CH:22][CH:23]=1)[CH3:16]>N1CCCCC1.C(O)C>[CH2:15]([O:17][C:18]1[CH:19]=[C:20]([C:24]2[CH:32]=[C:31]3[C:27]([C:28](=[CH:12][C:9]4[NH:8][C:7]([CH3:14])=[C:6]([CH2:5][CH2:4][C:1]([OH:3])=[O:2])[C:10]=4[CH3:11])[C:29](=[O:33])[NH:30]3)=[CH:26][CH:25]=2)[CH:21]=[CH:22][CH:23]=1)[CH3:16]

Participants

5

Reactant 2

HCID 15125203-(5-formyl-2,4-dimethyl-1H-pyrrol-3-yl)propanoic AcidHCID 106346366-(3-Ethoxyphenyl)indolin-2-one

Product 1

HCID 540626133-(5-[6-(3-Ethoxy-phenyl)-2-oxo-1,2-dihydroindol-3-ylidenemethyl]-2,4-dimethyl-1H-pyrrol-3-yl)-propionic acidYield 105.5%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Procedure

3-(2-carboxyethyl)-2,4-dimethyl-5-formylpyrrole (97.6 mg), 127 mg 6-(3-ethoxyphenyl)-2-oxindole, and 2 drops piperidine in 2 mL ethanol were heated at 90° C. overnight. The reaction mixture was cooled and concentrated. The residue was suspended in 6 N aqueous hydrochloric acid. The precipitate was filtered, washed with water to pH 6 and dried in a vacuum oven overnight to give 227 mg of the title compound (˜100%) as a brown solid.

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated
  3. filtrationThe precipitate was filtered
  4. washwashed with water to pH 6
  5. customdried in a vacuum oven overnight

Sources & evidence

ORD record
ord-2987f73e4aea4ae98b3cc9c353c8ab79
Source dataset
uspto-grants-2005_04
Patent number
US06878733B1

Reaction notes

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