Methyl iodide → methyl 4-((1-methyl-1H-indol-3-yl)methyl)benzoate

HRID 1163096Notes

Reaction equation

HRID 1163096 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C:11]2[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=2)=[CH:2]1.[H-].[Na+].[CH3:23]I>C1COCC1>[CH3:23][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C:11]2[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=2)=[CH:2]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 26367194methyl 4-((1H-indol-3-yl)methyl)benzoate

Product 1

HCID 58970761methyl 4-((1-methyl-1H-indol-3-yl)methyl)benzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of methyl 4-((1H-indol-3-yl)methyl)benzoate (0.250 g, 0.94 mmol) in THF is added dropwise to a suspension of NaH (0.048 g, 1.19 mmol) in THF. The mixture is stirred for 15 minutes, treated with methyl iodide (0.154 g, 1.08 mmol), stirred for 30 minutes and concentrated in vacuo. The resultant solid residue is partioned between CH2Cl2 and H2O. The organic phase is separated, dried over Na2SO4 and concentrated to dryness to yield methyl 4-((1-methyl-1H-indol-3-yl)methyl)benzoate.

Workup

  1. stirringstirred for 30 minutes
  2. concentrationconcentrated in vacuo
  3. customThe organic phase is separated
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-0c72bbc334f348298ae8a70e538aa13d
Source dataset
uspto-grants-2010_10
Patent number
US07820825B2

Reaction notes

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