ethyl 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylate → ethyl 2,4-dimethyl-5-[(2-oxo-1H-indol-3-ylidene)methyl]-1H-pyrrole-3-carboxylate

HRID 992468Notes

Reaction equation

HRID 992468 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].[CH2:11]([O:13][C:14]([C:16]1[C:17]([CH3:24])=[C:18]([CH:22]=O)[NH:19][C:20]=1[CH3:21])=[O:15])[CH3:12]>N1CCCCC1.C(O)C>[CH3:21][C:20]1[NH:19][C:18]([CH:22]=[C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][C:2]2=[O:10])=[C:17]([CH3:24])[C:16]=1[C:14]([O:13][CH2:11][CH3:12])=[O:15]

Participants

5

Reactant 2

HCID 137485ethyl 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylateHCID 321710Oxindole

Product 1

HCID 5654ethyl 2,4-dimethyl-5-[(2-oxo-1H-indol-3-ylidene)methyl]-1H-pyrrole-3-carboxylateYield 79%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

A reaction mixture of 134.0 mg of oxindole, 234.3 mg of the 4-ethoxycarbonyl-3,5-dimethylpyrrole-2-carboxaldehyde, and 3 drops of piperidine in 3 mL of ethanol was stirred at 90° C. for 3 h. After cooling, the precipitate was filtered, washed with cold ethanol, and dried to yield 244.6 mg (79%) of the title compound as a yellow solid.

Workup

  1. temperatureAfter cooling
  2. filtrationthe precipitate was filtered
  3. washwashed with cold ethanol
  4. customdried

Sources & evidence

ORD record
ord-1bf791e9800c491c9bc0734984809478
Source dataset
uspto-grants-2002_10
Patent number
US06469032B2

Reaction notes

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