Benzyl Bromide → 1-Benzyl-2-ethyl-4-methoxy-1H-indole

HRID 1795188Notes

Reaction equation

HRID 1795188 reaction equation
[CH2:1]([C:3]1[NH:4][C:5]2[C:10]([CH:11]=1)=[C:9]([O:12][CH3:13])[CH:8]=[CH:7][CH:6]=2)[CH3:2].[H-].[Na+].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C=O)C.O>[CH2:1]([C:3]1[N:4]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:5]2[C:10]([CH:11]=1)=[C:9]([O:12][CH3:13])[CH:8]=[CH:7][CH:6]=2)[CH3:2]

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 98556072-ethyl-4-methoxy-1H-indole

Product 1

HCID 99432411-Benzyl-2-ethyl-4-methoxy-1H-indoleYield 49%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2-Ethyl-4-methoxy-1H-indole (4.2 g, 24 mmol) is dissolved in 30 mL of DMF and 960 mg (24 mmol) of 60% NaH/minerial oil is added. After 1.5 hours, 2.9 mL(24 mmol) of benzyl bromide is added. After 4 hours, the mixture is diluted with water and extracted twice with ethyl acetate. The combined ethyl acetate is washed with brine, dried (MgSO4) and concentrated at reduced pressure. The residue is chromatographed on silica gel and eluted with 20% EtOAc/hexane to give 3.1 g (49% yield) of 2-ethyl-4-methoxy-1-(phenylmethyl)-1H-indole.

Workup

  1. waitAfter 4 hours
  2. extractionextracted twice with ethyl acetate
  3. washThe combined ethyl acetate is washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated at reduced pressure
  6. customThe residue is chromatographed on silica gel
  7. washeluted with 20% EtOAc/hexane

Sources & evidence

ORD record
ord-58813b829f9c4daca08f9a2e01027093
Source dataset
uspto-grants-2006_04
Patent number
US07026348B2

Reaction notes

Loading…