Methyl iodide → HCID 21938282, compound

HRID 1242130Notes

Reaction equation

HRID 1242130 reaction equation
[Na].[CH3:2]I.[Cl:4][C:5]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:6]=1[CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]([O:19][CH3:20])=[O:18])[CH:15]=2)[NH:10][CH:9]=1>CN(C)C=O>[Cl:4][C:5]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:6]=1[CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]([O:19][CH3:20])=[O:18])[CH:15]=2)[N:10]([CH3:2])[CH:9]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 5360545SodiumHCID 10131732HCID 10131732, compound

Product 1

HCID 21938282HCID 21938282, compoundYield 84.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

60% sodium hydlide (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-metoxycarbonylindole (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-577faa0b8c1740b99a8ce66700d567b1
Source dataset
uspto-grants-2006_10
Patent number
US07115647B2

Reaction notes

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