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Sodium hydride → 3-[(3,4-dimethoxy-phenyl)-(3,5-dimethyl-1H-pyrrol-2-yl)-methylene]-1,3-dihydro-indol-2-one

HRID 2120228
Notes
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Reaction equation

HRID 2120228 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([C:13]2[NH:14][C:15]([CH3:19])=[CH:16][C:17]=2[CH3:18])=O)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[NH:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22][C:21]1=[O:29].N1CCCC1.[H-].[Na+]>N12CCCN=C1CCCCC2.CN(C)C=O.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([C:13]2[NH:14][C:15]([CH3:19])=[CH:16][C:17]=2[CH3:18])=[C:22]2[C:23]3[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=3)[NH:20][C:21]2=[O:29])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 24758Sodium hydrideHCID 31268PyrrolidineHCID 321710OxindoleHCID 23439089(3,4-dimethoxy-phenyl)-(3,5-dimethyl-1H-pyrrol-2-yl)-methanone

Product 1

HCID 539061583-[(3,4-dimethoxy-phenyl)-(3,5-dimethyl-1H-pyrrol-2-yl)-methylene]-1,3-dihydro-indol-2-oneYield 3.3%

Reagents, catalysts & solvents 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneCatalyst
HCID 962WaterSolvent
HCID 6228DimethylformamideSolvent

Procedure

(3,4-Dimethoxy-phenyl)-(3,5-dimethyl-1H-pyrrol-2-yl)-methanone (100 mg, 0.4 mmol), oxindole (100 mg, 0.8 mmol), pyrrolidine (0.2 mL) and 1,8-diazabicyclo[5.4.0]undec-7-ene (a few drops) in dimethylforamide (1.5 mL) was heated at 160° C. for 2 hours. Sodium hydride (18 mg) was added to the reaction mixture and the heating was continued at 160° C. for 3 days. The reaction was poured into water and extracted with ethyl acetate. The organic layer was washed with water, dried and concentrated. The residue was chromatographed eluting with ethyl acetate and hexane to give 5 mg of 3-[(3,4-dimethoxy-phenyl)-(3,5-dimethyl-1H-pyrrol-2-yl)-methylene]-1,3-dihydro-indol-2-one. MS EI 374 [M]+.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was chromatographed
  6. washeluting with ethyl acetate and hexane

Sources & evidence

ORD record
ord-7260a3583a434f72b910d5777a6ab168
Source dataset
uspto-grants-2004_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06689806B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes