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

HRID 1243467Notes

Reaction equation

HRID 1243467 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].[CH3:15][O:16][C:17]1[CH:18]=[C:19]([C:23]2[CH:31]=[C:30]3[C:26]([CH2:27][C:28](=[O:32])[NH:29]3)=[CH:25][CH:24]=2)[CH:20]=[CH:21][CH:22]=1>N1CCCCC1.C(O)C>[CH3:15][O:16][C:17]1[CH:18]=[C:19]([C:23]2[CH:31]=[C:30]3[C:26]([C:27](=[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:28](=[O:32])[NH:29]3)=[CH:25][CH:24]=2)[CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 2

HCID 15125203-(5-formyl-2,4-dimethyl-1H-pyrrol-3-yl)propanoic AcidHCID 105860706-(3-Methoxyphenyl)-1,3-dihydroindol-2-one

Product 1

HCID 544755513-{5-[6-(3-Methoxy-phenyl)-2-oxo-1,2-dihydroindol-3-ylidenemethyl]-2,4-dimethyl-1H-pyrrol-3-yl}-propionic acidYield 91%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Procedure

3-(2-Carboxyethyl)-2,4-dimethyl-5-formylpyrrole (117 mg), 120 mg 6-(3-methoxyphenyl)-2-oxindole and 3 drops piperidine in 3 mL of 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 190 mg (91%) of the title compound 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-5423af29d6a24f818798ab1f8717e356
Source dataset
uspto-grants-2006_10
Patent number
US07119090B2

Reaction notes

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