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

HRID 3358

Reaction equation

HRID 3358 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-80c7b751a3284a8b966f0ea7134ae600
Source dataset
uspto-grants-1998_03
Patent number
US05733923

Linked notes

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