6-(3-Methoxyphenyl)-1,3-dihydroindol-2-one → 4-(2-Carboxyethyl)-5-[6-(3-methoxyphenyl)-2-oxo-1,2-dihydroindol-3-ylidenemethyl]-3-methyl-1H-pyrrole-2-carboxylic acid

HRID 24550

Reaction equation

C([O:3][C:4]([C:6]1[NH:7][C:8]([CH:19]=O)=[C:9]([CH2:12][CH2:13][C:14]([O:16]CC)=[O:15])[C:10]=1[CH3:11])=[O:5])C.[CH3:21][O:22][C:23]1[CH:24]=[C:25]([C:29]2[CH:37]=[C:36]3[C:32]([CH2:33][C:34](=[O:38])[NH:35]3)=[CH:31][CH:30]=2)[CH:26]=[CH:27][CH:28]=1>N1CCCCC1.C(O)C>[C:14]([CH2:13][CH2:12][C:9]1[C:10]([CH3:11])=[C:6]([C:4]([OH:3])=[O:5])[NH:7][C:8]=1[CH:19]=[C:33]1[C:32]2[C:36](=[CH:37][C:29]([C:25]3[CH:26]=[CH:27][CH:28]=[C:23]([O:22][CH3:21])[CH:24]=3)=[CH:30][CH:31]=2)[NH:35][C:34]1=[O:38])([OH:16])=[O:15]

Participants

Conditions

Temperature: 90 °C

Procedure

5-Formyl-4-(2-ethoxycarbonylethyl)-3-methyl-1H-pyrrole-2-carboxylic acid ethyl ester (281 mg), 6-(3-methoxy-phenyl)-2-oxindole (287 mg), and piperidine (2 drops) in ethanol (5 mL) were stirred at 90° C. overnight. The precipitate was filtered and washed with ethanol. The yellow orange solid and potassium hydroxide (4 pellets) were stirred in ethanol (3 mL) at 90° C. for 2.5 hours. The reaction mixture was cooled and concentrated. The residue was dissolved into water and acidified with 2 N hydrochloric acid to pH 2. The precipitate was filtered, washed with water, and dried in a vacuum oven overnight to give 413 mg of 4-(2-Carboxyethyl)-5-[6-(3-methoxyphenyl)-2-oxo-1,2-dihydroindol-3-ylidenemethyl]-3-methyl-1H-pyrrole-2-carboxylic acid

Workup

filtrationThe precipitate was filtered
washwashed with ethanol
temperatureThe reaction mixture was cooled
concentrationconcentrated
dissolutionThe residue was dissolved into water
filtrationThe precipitate was filtered
washwashed with water
customdried in a vacuum oven overnight

Sources & evidence

ORD record: ord-a4195a0932a748d4ba0033ecb630ebd4
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06855730B2

Linked notes

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