N-Methyloxindole → 4-Methyl-5-(1-methyl-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-1H-pyrrole-2-carboxylic acid

Reaction equation

[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C:3]1=[O:11].[CH:12]([C:14]1[NH:18][C:17]([C:19]([OH:21])=[O:20])=[CH:16][C:15]=1[CH3:22])=O>>[CH3:22][C:15]1[CH:16]=[C:17]([C:19]([OH:21])=[O:20])[NH:18][C:14]=1[CH:12]=[C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:2]([CH3:1])[C:3]1=[O:11]

Participants

Reactant 2

HCID 6096N-Methyloxindole

HCID 98988845-formyl-4-methyl-1H-pyrrole-2-carboxylic Acid

Product 1

HCID 672815544-Methyl-5-(1-methyl-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-1H-pyrrole-2-carboxylic acidYield 88.6%

Procedure

1-Methyl-1,3-dihydroindol-2-one (147 mg, 1 mmol) was condensed with 5-formyl-4-methyl-1H-pyrrole-2-carboxylic acid (153 mg) using method D to give 250 mg (86%) of the title compound.

Sources & evidence

ORD record: ord-4837b91275164d1fba31a8683e4cee84
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07125905B2

Reaction notes

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