Hexane → 1-[(2,6-dichlorophenyl)methyl]-4-methoxy-2-methyl-1H-indole

HRID 566653Notes

Reaction equation

HRID 566653 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.Cl[CH2:22][C:23]1[C:28]([Cl:29])=[CH:27][CH:26]=[CH:25][C:24]=1[Cl:30]>CN(C=O)C.O>[Cl:29][C:28]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:30])[C:23]=1[CH2:22][N:7]1[C:8]2[C:4](=[C:3]([O:2][CH3:1])[CH:11]=[CH:10][CH:9]=2)[CH:5]=[C:6]1[CH3:12]

Participants

7

Reactant 4

HCID 8058HexaneHCID 24758Sodium hydrideHCID 748322,6-Dichlorobenzyl chlorideHCID 107732744-methoxy-2-methyl-1H-indole

Product 1

HCID 107819381-[(2,6-dichlorophenyl)methyl]-4-methoxy-2-methyl-1H-indoleYield 84.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

4-Methoxy-2-methyl-1H-indole (805 mg, 5 mmol) was added to a mixture of 160 mg (4 mmol) of 60% sodium hydride/mineral oil (washed with hexane before adding DMF) in 10 mL of DMF and after stirring for 0.67 hours, 782 mg (4 mmol) of α,2,6-trichlorotoluene was added. The mixture was stirred at room temperature for 5 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 1.08 g (84% yield) of 1-[(2,6-dichlorophenyl)methyl]-4-methoxy-2-methyl-1H-indole, melting at 154-157° C.

Workup

  1. stirringThe mixture was stirred at room temperature for 5 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-ed680c7681c3407a95cd218a976adc82
Source dataset
uspto-grants-2001_01
Patent number
US06175021B1

Reaction notes

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