Sodium Chloride → HCID 12050027, compound

HRID 1582223Notes

Reaction equation

HRID 1582223 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([CH3:23])=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:26]I.[Cl-].[Na+]>CN(C)C=O>[CH2:1]([O:8][C:9]1[C:10]([CH3:23])=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH3:26])[C:13]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:12]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 12050026HCID 12050026, compound

Product 1

HCID 12050027HCID 12050027, compoundYield 96.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of ethyl 5-benzyloxy-4-methyl-1H-indole-2-carboxylate (3.50 g, 11.3 mmol), 60% sodium hydride (0.45 g, 11.3 mmol) and N,N-dimethylformamide (70 ml) was stirred at room temperature for 30 minutes, and then methyl iodide (3.21 g, 22.6 mmol) was added dropwise thereto, followed by stirring at room temperature for another 2.5 hours. The reaction mixture was poured into a 5% aqueous sodium chloride solution and extracted twice with ethyl acetate, and the extract solution was washed with a 5% aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent:ethyl acetate/n-hexane=3/97) to obtain 3.53 g of ethyl 5-benzyloxy-1,4-dimethyl-1H-indole-2-carboxylate.

Workup

  1. stirringby stirring at room temperature for another 2.5 hours
  2. extractionextracted twice with ethyl acetate
  3. washthe extract solution was washed with a 5% aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe resulting residue was purified by a silica gel column chromatography (eluent:ethyl acetate/n-hexane=3/97)

Sources & evidence

ORD record
ord-7a17dc34e33e44d08cc57033f1fb3eca
Source dataset
uspto-grants-2004_05
Patent number
US06734205B2

Reaction notes

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