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

HRID 2303473Notes

Reaction equation

HRID 2303473 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.[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>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[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 107732744-methoxy-2-methyl-1H-indole

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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. washof 60% sodium hydride/mineral oil (washed with hexane before adding DMF) in 15 mL of DMF
  2. stirringThe mixture was stirred at room temperature for 18 hours
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate solution was washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationafter concentrating at reduced pressure
  7. customthe residue was chromatographed on silica gel eluting with 20% EtOAc/hexane

Sources & evidence

ORD record
ord-b9b0a893a5a54194806f8ca30eaaeccb
Source dataset
uspto-grants-2002_08
Patent number
US06433001B1

Reaction notes

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