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Methyl iodide → 2-[1-(4-chlorobenzyl)-1H-indol-3-yl]-N-methyl-2-oxo-N-(5-oxo-2,5-dihydro 3-furanyl)acetamide

HRID 353476
Notes
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Reaction equation

HRID 353476 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:30]=[CH:29][C:7]([CH2:8][N:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([C:18](=[O:28])[C:19]([NH:21][C:22]3[CH2:23][O:24][C:25](=[O:27])[CH:26]=3)=[O:20])=[CH:10]2)=[CH:6][CH:5]=1.[CH3:31]I>CN(C=O)C>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][N:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([C:18](=[O:28])[C:19]([N:21]([CH3:31])[C:22]3[CH2:23][O:24][C:25](=[O:27])[CH:26]=3)=[O:20])=[CH:10]2)=[CH:29][CH:30]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 101574932-[1-(4-chlorobenzyl)-1H-indol-3-yl]-2-oxo-N-(5-oxo-2,5-dihydro-3-furanyl)acetamide

Product 1

HCID 235139812-[1-(4-chlorobenzyl)-1H-indol-3-yl]-N-methyl-2-oxo-N-(5-oxo-2,5-dihydro 3-furanyl)acetamide

Reagents, catalysts & solvents 1

HCID 6228Dimethylformamide
Solvent

Procedure

Under nitrogen atmosphere, sodium hydride (10 mg of a 60% wt/wt suspension in mineral oil) is added to a solution of 2-[1-(4-chlorobenzyl)-1H-indol-3-yl]-2-oxo-N-(5-oxo-2,5-dihydro-3-furanyl)acetamide (100 mg) in dry DMF (2 ml). After 20′, methyl iodide (0.016 ml) is added. After 3 h the solvent is removed by roto-evaporation and the obtained residue is partitioned between water and ethyl acetate. The organic layer is dried over sodium sulfate and concentrated to dryness. The obtained residue is suspended in boiling MeOH/i-PrOH 1/1. After cooling to room temperature the insoluble material is collected by filtration and oven-dried at 60° C. for 3 h, to give 2-[1-(4-chlorobenzyl)-1H-indol-3-yl]-N-methyl-2-oxo-N-(5-oxo-2,5-dihydro 3-furanyl)acetamide (52 mg).

Workup

  1. customAfter 3 h the solvent is removed by roto-evaporation
  2. customthe obtained residue is partitioned between water and ethyl acetate
  3. dry with materialThe organic layer is dried over sodium sulfate
  4. concentrationconcentrated to dryness
  5. filtrationis collected by filtration
  6. customoven-dried at 60° C. for 3 h

Sources & evidence

ORD record
ord-546348ecf37042469893d45e7a0da368
Source dataset
uspto-grants-2004_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06753342B2

Reaction notes

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