Hexane → 1-[(4-fluorophenyl)methyl]-4-methoxy-2-methyl-1H-indole

HRID 566657

Reaction equation

HRID 566657 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.[F:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26]Cl)=[CH:24][CH:23]=1>CN(C=O)C.O>[F:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26][N:7]2[C:8]3[C:4](=[C:3]([O:2][CH3:1])[CH:11]=[CH:10][CH:9]=3)[CH:5]=[C:6]2[CH3:12])=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 8058HexaneHCID 96024-Fluorobenzyl chlorideHCID 24758Sodium hydrideHCID 107732744-methoxy-2-methyl-1H-indole

Product 1

HCID 108258491-[(4-fluorophenyl)methyl]-4-methoxy-2-methyl-1H-indoleYield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

4-Methoxy-2-methyl-1H-indole (805 mg, 5 mmol) was added to a mixture of 200 mg (5 mmol) of 60% sodium hydride/mineral oil (washed with hexane before adding DMF) in 10 mL of DMF and after stirring for 0.5 hours, 0.6 mL (5 mmol) of 4-fluorobenzyl chloride 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 1.1 g (84% yield) of 1-[(4-fluorophenyl)methyl]-4-methoxy-2-methyl-1H-indole, melting at 104-108° C.

Workup

  1. stirringThe mixture was stirred at room temperature for 18 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-fb23ef7302ec4aaba9d124d7348ff685
Source dataset
uspto-grants-2001_01
Patent number
US06175021B1

Linked notes

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