Water → ethyl 1-methyl-6-(4-methylphenyl)-1H-indole-2-carboxylate

HRID 1169357Notes

Reaction equation

HRID 1169357 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:16]=[C:15]3[C:11]([CH:12]=[C:13]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[NH:14]3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[H-].[Na+].[CH3:24]I.O>CN(C=O)C>[CH3:24][N:14]1[C:15]2[C:11](=[CH:10][CH:9]=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=3)[CH:16]=2)[CH:12]=[C:13]1[C:17]([O:19][CH2:20][CH3:21])=[O:18]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 22990151ethyl 6-(4-methylphenyl)-1H-indole-2-carboxylate

Product 1

HCID 22989974ethyl 1-methyl-6-(4-methylphenyl)-1H-indole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Into a solution of ethyl 6-(4-methylphenyl)-1H-indole-2-carboxylate (0.9 g) in DMF (10 ml) was added at 0° C. sodium hydride (60%, 0.14 g), and the resulting mixture was stirred for 15 minutes. Into the reaction mixture was added methyl iodide (0.22 ml), and the resulting mixture was stirred at room temperature for 3 hours. The reaction mixture was mixed with water and was extracted with ethyl acetate. The organic layer was washed with an aqueous saturated solution of sodium chloride and was dried with magnesium sulfate. After concentration of the organic layer under reduced pressure, the residue was subjected to separation and purification using column chromatography (ethyl acetate/hexane 1:4) and further to recrystallization (ethyl acetate/hexane) to obtain ethyl 1-methyl-6-(4-methylphenyl)-1H-indole-2-carboxylate (0.80 g) as colorless crystals.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 3 hours
  2. extractionwas extracted with ethyl acetate
  3. washThe organic layer was washed with an aqueous saturated solution of sodium chloride
  4. dry with materialwas dried with magnesium sulfate
  5. customAfter concentration of the organic layer under reduced pressure, the residue was subjected to separation and purification
  6. customfurther to recrystallization (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-bee2b11e85394f9ba4d2156810c02790
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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