Benzyl Bromide → HCID 11471086, compound

HRID 2394447Notes

Reaction equation

HRID 2394447 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C)C=O>[CH2:16]([N:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 2737635methyl 1H-indole-5-carboxylate

Product 1

HCID 11471086HCID 11471086, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl indole-5-carboxylate (1.40 g) was dissolved in 10 ml of dimethylformamide, followed by addition of 212 mg of sodium hydride (content: 95%) under ice-cooling and stirring for one hour. To the mixture, there was added 1.51 g of benzyl bromide, followed by stirring the mixture for 2 hours, pouring the reaction solution into 140 ml of a 5% ammonium chloride aqueous solution and extraction with ethyl acetate (50 ml×2). The resulting organic phase was washed with water (50 ml×2), dried over anhydrous sodium sulfate and the solvent was removed through evaporation under reduced pressure to give 2.09 g of methyl 1-benzylindole-5-carboxylate as orange-colored crystals. The yield thereof was found to be 99%.

Workup

  1. temperaturecooling
  2. stirringby stirring the mixture for 2 hours
  3. additionpouring the reaction solution
  4. extractioninto 140 ml of a 5% ammonium chloride aqueous solution and extraction with ethyl acetate (50 ml×2)
  5. washThe resulting organic phase was washed with water (50 ml×2)
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was removed through evaporation under reduced pressure

Sources & evidence

ORD record
ord-39c880e5c1df4074ba927d63b8b832b7
Source dataset
uspto-grants-1998_09
Patent number
US05811439

Reaction notes

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