Benzyl Bromide → 2-ethyl-5-methoxy-1-(phenylmethyl)-1H-indole

HRID 3383Notes

Reaction equation

HRID 3383 reaction equation
[CH2:1]([C:3]1[NH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([O:12][CH3:13])=[CH:7][CH:6]=2)[CH3:2].C1COCC1.[H-].[Na+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN(C=O)C.O>[CH2:1]([C:3]1[N:4]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([O:12][CH3:13])=[CH:7][CH:6]=2)[CH3:2]

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 107024052-ethyl-5-methoxy-1H-indole

Product 1

HCID 105158362-ethyl-5-methoxy-1-(phenylmethyl)-1H-indoleYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2-Ethyl-5-methoxy-1H-indole (5.6 g, 21.5 mmol) was dissolved in 150 mL of DMF and 20 mL of THF and 1.0 g (25 mmol) of 60% sodium hydride was added. After stirring for 0.17 hours, 3.0 mL (25 mmol) of benzyl bromide was added. The mixture was stirred at room temperature for 10 hours, diluted with water and extracted with ethyl acetate. The ethyl acetate solution was washed with water, saturated NaCl solution, and dried (Na2 SO4). The EtOAc was evaporated and the residue was chromatographed on silica gel eluting with a gradient, 5% EtOAc/hexane→15% EtOAc/hexane to give 4.6 g (82% yield) of 2-ethyl-5-methoxy-1-(phenylmethyl)-1H-indole.

Workup

  1. stirringThe mixture was stirred at room temperature for 10 hours
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate solution was washed with water, saturated NaCl solution
  4. customdried (Na2 SO4)
  5. customThe EtOAc was evaporated
  6. customthe residue was chromatographed on silica gel eluting with a gradient, 5% EtOAc/hexane→15% EtOAc/hexane

Sources & evidence

ORD record
ord-58e3159b6ca6432dae5a788f94e6f3a6
Source dataset
uspto-grants-1998_03
Patent number
US05733923

Reaction notes

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