Methyl iodide → HCID 86659885, compound

HRID 2360164Notes

Reaction equation

HRID 2360164 reaction equation
[CH2:1]([N:4]([CH2:19][CH2:20][CH3:21])[C:5]([CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH3:18])[CH:15]=2)[NH:10][CH:9]=1)=[O:6])[CH2:2][CH3:3].[H-].[Na+].[CH3:24]I>CN(C)C=O.C(OCC)C>[CH2:19]([N:4]([CH2:1][CH2:2][CH3:3])[C:5]([CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH3:18])[CH:15]=2)[N:10]([CH3:24])[CH:9]=1)=[O:6])[CH2:20][CH3:21]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86659884HCID 86659884, compound

Product 1

HCID 86659885HCID 86659885, compoundYield 67.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(di-n-propylaminocarbonylmethyl)-5-methoxyindole (180 mg, 0.62 mmol) in 1.8 mL of N,N-dimethylformamide was added sodium hydride (55%, 40 mg, 0.93 mmol) at 0° C. After the reaction mixture was stirred at the same temperature for 30 min, methyl iodide (0.10 mL, 1.2 mmol) was added with additional stirring at room temperature for 12 h. After the reaction mixture was diluted with diethyl ether, and washed with water and brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5 to 80/20) to obtain the title compound (126 mg, 67%).

Workup

  1. stirringwith additional stirring at room temperature for 12 h
  2. washwashed with water and brine
  3. dry with materialdried over MgSO4
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated in vacuo
  6. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5 to 80/20)

Sources & evidence

ORD record
ord-d92132542bca43089f2581f8e0f8f4f3
Source dataset
uspto-grants-2014_04
Patent number
US08686024B2

Reaction notes

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