Sodium hydride → 1-[p-(2-Ethoxycarbonylpropen-1-yl)benzyl]-3-methyl-2-(3-pyridyl)indole

HRID 1633144Notes

Reaction equation

HRID 1633144 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]=1[C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1.[H-].[Na+].Cl[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([CH:27]=[C:28]([CH3:34])[C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:23][CH:22]=1>CN(C=O)C.O>[CH2:32]([O:31][C:29]([C:28]([CH3:34])=[CH:27][C:24]1[CH:25]=[CH:26][C:21]([CH2:20][N:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[C:2]([CH3:1])=[C:3]2[C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[CH:22][CH:23]=1)=[O:30])[CH3:33]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 155913683-Methyl-2-(3-pyridyl)indoleHCID 54424967Ethyl 3-(p-chloromethylphenyl)-2-methylacrylate

Product 1

HCID 545556371-[p-(2-Ethoxycarbonylpropen-1-yl)benzyl]-3-methyl-2-(3-pyridyl)indole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent3×

Procedure

A solution of 3-methyl-2-(3-pyridyl)indole (2.08 g) in 12 ml of DMF is added to a suspension of 0.528 g of 50% sodium hydride (dispersion in mineral oil) in 6 ml of DMF under nitrogen at 10°-15°. After complete addition the mixture is stirred at room temperature for 0.5 hour and is treated with a solution of 2.39 g of ethyl 3-(p-chloromethylphenyl)-2-methylacrylate in 5 ml of DMF dropwise. The resulting mixture is stirred at room temperature overnight and poured in 100 ml of water. The resulting mixture is extracted with ethyl acetate (2×50 ml) and the organic layer is washed with 100 ml of brine, dried over magnesium sulfate and evaporated to yield 1-[p-(2-ethoxycarbonylpropen-1-yl)benzyl]-3-methyl-2-(3-pyridyl)indole.

Workup

  1. additionAfter complete addition the mixture
  2. stirringThe resulting mixture is stirred at room temperature overnight
  3. extractionThe resulting mixture is extracted with ethyl acetate (2×50 ml)
  4. washthe organic layer is washed with 100 ml of brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-0dc0cc51016f4d659744ea65d9e296fb
Source dataset
uspto-grants-1984_10
Patent number
US04478842

Reaction notes

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