Water → 1-(2,4-Dichlorobenzyl)-6-(methoxycarbonyl)-3-methylindole

HRID 2187751Notes

Reaction equation

HRID 2187751 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([C:9]([CH3:14])=[CH:10][NH:11]2)=[CH:7][CH:6]=1)=[O:4].[H-].[Na+].[Cl:17][C:18]1[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:19]=1[CH2:20]Cl.O>CN(C)C=O>[Cl:17][C:18]1[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:19]=1[CH2:20][N:11]1[C:12]2[C:8](=[CH:7][CH:6]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[CH:13]=2)[C:9]([CH3:14])=[CH:10]1

Participants

6

Reactant 4

HCID 962WaterHCID 72122,4-Dichlorobenzyl chlorideHCID 24758Sodium hydrideHCID 21938240Methyl 3-methyl-1H-indole-6-carboxylate

Product 1

HCID 219382751-(2,4-Dichlorobenzyl)-6-(methoxycarbonyl)-3-methylindoleYield 79.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-(Methoxycarbonyl)-3-methylindole (0.57 g) is dissolved in N,N-dimethylformamide (10 ml), to which is added sodium hydride (60% oily, 0.145 g) with cooling with ice. Then, 2,4-dichlorobenzyl chloride (0.707 g) is added thereto, and stirred at room temperature for 1.5 hours. Water is added to the reaction mixture, which is then extracted with ethyl acetate. The organic layer is washed with a saturated saline solution, and dried with anhydrous magnesium sulfate. The drying agent is removed through filtration, and the filtrate is concentrated under reduced pressure. The resulting residue is purified through silica gel column chromatography (eluent: hexane/ethyl acetate=9/1) to obtain 1-(2,4-dichlorobenzyl)-6-(methoxycarbonyl)-3-methylindole (72) (0.83 g).

Workup

  1. temperaturewith cooling with ice
  2. extractionis then extracted with ethyl acetate
  3. washThe organic layer is washed with a saturated saline solution
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customThe drying agent is removed through filtration
  6. concentrationthe filtrate is concentrated under reduced pressure
  7. customThe resulting residue is purified through silica gel column chromatography (eluent: hexane/ethyl acetate=9/1)

Sources & evidence

ORD record
ord-c6749de8511143399a13f896bea062f3
Source dataset
uspto-grants-2002_06
Patent number
US06410584B1

Reaction notes

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