1-Chloromethylnaphthalene → 4-methoxy-2-methyl-1-[(1-naphthalenyl)methyl]-1H-indole

HRID 2303496Notes

Reaction equation

HRID 2303496 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+].Cl[CH2:16][C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=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[CH2:16][C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 68451-ChloromethylnaphthaleneHCID 24758Sodium hydrideHCID 107732744-methoxy-2-methyl-1H-indole

Product 1

HCID 106380394-methoxy-2-methyl-1-[(1-naphthalenyl)methyl]-1H-indoleYield 97.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

4-Methoxy-2-methyl-1H-indole (644 mg, 4 mmol) was dissolved in 10 mL of DMF and 160 mg (4 mmol) of 60% NaH/mineral oil was added. After 0.67 hours, 707 mg (4 mmol) of 1-(chloromethyl)naphthalene was added. After 5 hours, the mixture was diluted with water and extracted twice with ethyl acetate. The combined ethyl acetate was washed with brine, dried (MgSO4) and concentrated at reduced pressure. The residue was chromatographed on silica gel and eluted with 20% EtOAc/hexane to give 1.17 g (97% yield) of 4-methoxy-2-methyl-1-[(1-naphthalenyl)methyl]-1H-indole.

Workup

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

Sources & evidence

ORD record
ord-eac4735b7e1c4ef5a563aea1f303d957
Source dataset
uspto-grants-2002_08
Patent number
US06433001B1

Reaction notes

Loading…