5-Phenyloxindole → 2,4-Dimethyl-5-(2-oxo-5-Phenyl-1,2-Dihydroindol-3-Ylidenemethyl)-1H-Pyrrole-3-Carboxylic Acid (3-Dimethylaminopropyl) Amide

HRID 1368463Notes

Reaction equation

[C:1]1([C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][CH:15]=2)[NH:12][C:11](=[O:16])[CH2:10]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:17][N:18]([CH3:34])[CH2:19][CH2:20][CH2:21][NH:22][C:23]([C:25]1[C:29]([CH3:30])=[C:28]([CH:31]=O)[NH:27][C:26]=1[CH3:33])=[O:24]>>[CH3:34][N:18]([CH3:17])[CH2:19][CH2:20][CH2:21][NH:22][C:23]([C:25]1[C:29]([CH3:30])=[C:28]([CH:31]=[C:10]2[C:9]3[C:13](=[CH:14][CH:15]=[C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[CH:8]=3)[NH:12][C:11]2=[O:16])[NH:27][C:26]=1[CH3:33])=[O:24]

Participants

Reactant 2

HCID 133019785-Phenyloxindole

HCID 865862095-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (3-dimethylaminopropyl)amide

Product 1

HCID 672808772,4-Dimethyl-5-(2-oxo-5-Phenyl-1,2-Dihydroindol-3-Ylidenemethyl)-1H-Pyrrole-3-Carboxylic Acid (3-Dimethylaminopropyl) AmideYield 28.2%

Procedure

5-Phenyl-1,3-dihydroindol-2-one (67 mg, 0.32 mmol) was condensed with 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (3-dimethylaminopropyl)amide (81 mg) to give 40 mg (28%) of the title compound as an orange solid.

Sources & evidence

ORD record: ord-e22bcca346434700a20cb54cdcfdd545
Source dataset: uspto-grants-2003_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06573293B2

Reaction notes

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