Methyl iodide → Ethyl 6-benzyloxy-4-chloro-1-methyl-2-indolecarboxylate

HRID 1067781Notes

Reaction equation

HRID 1067781 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[C:14]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[NH:15]2)=[C:11]([Cl:23])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:26]I>CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[C:14]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[N:15]2[CH3:26])=[C:11]([Cl:23])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 21714295Ethyl 6-(benzyloxy)-4-chloro-1H-indole-2-carboxylate

Product 1

HCID 21194606Ethyl 6-benzyloxy-4-chloro-1-methyl-2-indolecarboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

After 3.70 g (11.2 mmol) of ethyl 6-benzyloxy-4-chloro-2-indolecarboxylate was added to a suspension of 0.45 g (11.2 mmol) of 60% sodium hydride in 70 ml of dimethylformamide, the mixture was stirred at room temperature. After the mixture became an almost transparent solution, a solution of 3.18 g (22.4 mmcol) of methyl iodide in 10 ml of dimethylformamide was dropwise added to the transparent solution at room temperature followed by stirring for 5 hours at the same temperature. The reaction solution was poured onto ice water. The resulting mixture was then extracted three times with ethyl acetate and the combined extracts were washed with water. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure and the residue was isolated and purified by silica gel column chromatography to give 3.72 (96.4%) of ethyl 6-benzyloxy-4-chloro-1-methyl-2-indolecarboxylate.

Workup

  1. stirringby stirring for 5 hours at the same temperature
  2. additionThe reaction solution was poured onto ice water
  3. extractionThe resulting mixture was then extracted three times with ethyl acetate
  4. washthe combined extracts were washed with water
  5. dry with materialAfter drying over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customthe residue was isolated
  8. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-2cfe5555107642f1994d11ed065cc4fa
Source dataset
uspto-grants-2001_06
Patent number
US06248772B1

Reaction notes

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