Water → 3-[5-(6-Hydroxy-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-4-methyl-1H-pyrrol-3-yl]-propionic acid 3,5-dimethoxy-benzyl ester

HRID 1243464Notes

Reaction equation

HRID 1243464 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](=[CH:12][C:13]3[NH:17][CH:16]=[C:15]([CH2:18][CH2:19][C:20]([OH:22])=[O:21])[C:14]=3[CH3:23])[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[CH3:24][O:25][C:26]1[CH:27]=[C:28]([CH:31]=[C:32]([O:34][CH3:35])[CH:33]=1)[CH2:29]Cl.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:35][O:34][C:32]1[CH:31]=[C:28]([CH:27]=[C:26]([O:25][CH3:24])[CH:33]=1)[CH2:29][O:21][C:20](=[O:22])[CH2:19][CH2:18][C:15]1[C:14]([CH3:23])=[C:13]([CH:12]=[C:6]2[C:5]3[C:9](=[CH:10][C:2]([OH:1])=[CH:3][CH:4]=3)[NH:8][C:7]2=[O:11])[NH:17][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27583953,5-Dimethoxybenzyl chlorideHCID 572383163-[5-(6-Hydroxy-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-4-methyl-1H-pyrrol-3-yl]-propionic acid

Product 1

HCID 690327253-[5-(6-Hydroxy-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-4-methyl-1H-pyrrol-3-yl]-propionic acid 3,5-dimethoxy-benzyl esterYield 28.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-[5-(6-Hydroxy-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-4-methyl-1H-pyrrol-3-yl]-propionic acid (100 mg), 56 mg 3,5-dimethoxy- benzylchloride and 207 mg potassium carbonate in 2 mL anhydrous dimethylformamide were heated at 90° C. overnight. The reaction mixture was cooled, poured into water and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate, and concentrated. The crude product was purified by chromatography on a silica gel column eluting with ethyl acetate-hexane-acetic acid to give 39 mg of the title compound as a brown solid.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe crude product was purified by chromatography on a silica gel column
  7. washeluting with ethyl acetate-hexane-acetic acid

Sources & evidence

ORD record
ord-58964bfbc0fc4c19890227179be5877c
Source dataset
uspto-grants-2006_10
Patent number
US07119090B2

Reaction notes

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