Methyl iodide → HCID 23159912, compound

HRID 2110882Notes

Reaction equation

HRID 2110882 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[CH:11]=[C:12]([CH:27]=[CH:28][CH:29]=3)[CH2:13][O:14][C:15]3[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][C:23]([O:25][CH3:26])=[O:24])=[CH:17][CH:16]=3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.IC.[C:32](=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[CH3:32][N:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[CH:11]=[C:12]([CH:27]=[CH:28][CH:29]=3)[CH2:13][O:14][C:15]3[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][C:23]([O:25][CH3:26])=[O:24])=[CH:17][CH:16]=3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 23159928HCID 23159928, compound

Product 1

HCID 23159912HCID 23159912, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of methyl 3-(4-{[3-(1H-indol-5-yl)benzyl]oxy]phenyl)propanoate (0.40 g, 1.04 mmol), iodomethane (0.18 mL, 2.89 mmol) and potassium carbonate (0.50 g, 3.62 mmol) in N,N-dimethylformamide (20 mL) was stirred at room temperature for 4 days. The reaction solution was diluted with ethyl acetate, and the mixture washed successively with aqueous citric acid solution, water and aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (ethyl acetate:hexane=1:5-1:3-1:2) to give the title compound (0.23 g, yield 56%) as colorless prism crystals. MS: m/z 400 (MH+).

Workup

  1. washthe mixture washed successively with aqueous citric acid solution, water and aqueous sodium chloride solution
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0f377316a0384a3f8d529d820c3e8229
Source dataset
uspto-grants-2009_04
Patent number
US07517910B2

Reaction notes

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