Methyl iodide → HCID 21938282, compound

HRID 2187740Notes

Reaction equation

HRID 2187740 reaction equation
[H-].[Na+].[CH3:3]I.[Cl:5][C:6]1[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:7]=1[CH2:8][C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:18]([O:20][CH3:21])=[O:19])[CH:16]=2)[NH:11][CH:10]=1>CN(C)C=O>[Cl:5][C:6]1[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:7]=1[CH2:8][C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:18]([O:20][CH3:21])=[O:19])[CH:16]=2)[N:11]([CH3:3])[CH:10]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 10131732HCID 10131732, compound

Product 1

HCID 21938282HCID 21938282, compoundYield 84.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

60% sodium hydride (0.07 g) and then methyl iodide (0.18 g) are added in that order to an N,N-dimethylformamide solution of 3-(2,4-dichlorobenzyl)-5-methoxycarbonylindole (0.34 g), and stirred at room temperature for 19 hours. After concentrated under reduced pressure, this is extracted with water and ethyl acetate. The resulting extract is washed with water, dried, concentrated, and purified through silica gel column chromatography (eluent: hexane/ethyl acetate=9/1 to 7/1) to obtain 3-(2,4-dichlorobenzyl)-5-methoxycarbonyl-1-methylindole (55) (0.30 g).

Workup

  1. concentrationAfter concentrated under reduced pressure
  2. extractionthis is extracted with water and ethyl acetate
  3. extractionThe resulting extract
  4. washis washed with water
  5. customdried
  6. concentrationconcentrated
  7. custompurified through silica gel column chromatography (eluent: hexane/ethyl acetate=9/1 to 7/1)

Sources & evidence

ORD record
ord-884153bb83fe4324bd0075b276a0ba3d
Source dataset
uspto-grants-2002_06
Patent number
US06410584B1

Reaction notes

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