2-Methyl-3-carbethoxy-4-(3-propionic acid)pyrrole → 4-(2-Carboxyethyl)-5-[6-(4-fluorophenyl)-2-oxo-1,2-dihydro-indol-3-ylidenemethyl]-2-methyl-1H-pyrrole-3-carboxylic Acid Ethyl Ester

HRID 24469Notes

Reaction equation

HRID 24469 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:16]=[C:15]3[C:11]([CH2:12][C:13](=[O:17])[NH:14]3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH2:18]([O:20][C:21]([C:23]1[C:27]([CH2:28][CH2:29][C:30]([OH:32])=[O:31])=[C:26]([CH:33]=O)[NH:25][C:24]=1[CH3:35])=[O:22])[CH3:19].C(CCC1C(C(OCC)=O)=C(C)NC=1)(O)=O>>[CH2:18]([O:20][C:21]([C:23]1[C:27]([CH2:28][CH2:29][C:30]([OH:32])=[O:31])=[C:26]([CH:33]=[C:12]2[C:11]3[C:15](=[CH:16][C:8]([C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=4)=[CH:9][CH:10]=3)[NH:14][C:13]2=[O:17])[NH:25][C:24]=1[CH3:35])=[O:22])[CH3:19]

Participants

4

Reactant 3

HCID 217287442-Methyl-3-carbethoxy-4-(3-propionic acid)pyrroleHCID 220421726-(4-Fluorophenyl)-1,3-dihydro-2H-indol-2-oneHCID 545693914-(2-carboxyethyl)-5-formyl-2-methyl-1H-pyrrole-3-carboxylic acid ethyl ester

Product 1

HCID 697640874-(2-Carboxyethyl)-5-[6-(4-fluorophenyl)-2-oxo-1,2-dihydro-indol-3-ylidenemethyl]-2-methyl-1H-pyrrole-3-carboxylic Acid Ethyl Ester

Procedure

6-(4-Fluorophenyl)-1,3-dihydroindol-2-one (60 mg, 0.26 mmol) was condensed with 4-(2-carboxyethyl)-5-formyl-2-methyl-1H-pyrrole-3-carboxylic acid ethyl ester (65 mg), prepared by formylation of 4-(2-carboxyethyl)-3-ethoxycarbonyl-2-methylpyrrole (Bulter, A. R., and George, S. D. (1993) Tetrahedron 49: 7017-7026), to give the title compound.

Sources & evidence

ORD record
ord-5cc4671342e249388623d4d7d8b97aa7
Source dataset
uspto-grants-2005_02
Patent number
US06855730B2

Reaction notes

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