Benzyl Bromide → 4-methoxy-2-methyl-1-(phenylmethyl)-1H-indole

HRID 650508Notes

Reaction equation

HRID 650508 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[C:6]([CH3:12])[NH:7]2.[H-].[Na+].CCCCCC.[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN(C=O)C.O>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[C:6]([CH3:12])[N:7]2[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 8058HexaneHCID 24758Sodium hydrideHCID 107732744-methoxy-2-methyl-1H-indole

Product 1

HCID 107771474-methoxy-2-methyl-1-(phenylmethyl)-1H-indoleYield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

4-Methoxy-2-methyl-1H-indole (1 g, 6.2 mmol) was added to 248 mg (6.2 mmol) of 60% sodium hydride/mineral oil (washed with hexane before adding DMF) in 15 mL of DMF and after stirring for 0.5 hour, 0.74 mL (6.2 mmol) of benzyl bromide was added. The mixture was stirred at room temperature for 18 hours, diluted with water and extracted with ethyl acetate. The ethyl acetate solution was washed with brine, dried (MgSO4) and after concentrating at reduced pressure, the residue was chromatographed on silica gel eluting with 20% EtOAc/hexane to give 1.3 g(84% yield) of 4-methoxy-2-methyl-1-(phenylmethyl)-1H-indole, melting at 96-116° C.

Workup

  1. stirringThe mixture was stirred at room temperature for 18 hours
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate solution was washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationafter concentrating at reduced pressure
  6. customthe residue was chromatographed on silica gel eluting with 20% EtOAc/hexane

Sources & evidence

ORD record
ord-ccc01937fddc4eadbe961954a2bae38a
Source dataset
uspto-grants-2001_08
Patent number
US06274578B1

Reaction notes

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