Methyl iodide → 5-Fluoro-1,3-dimethyl-1H-indole

HRID 1693134Notes

Reaction equation

HRID 1693134 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH3:11].[OH-].[K+].I[CH3:15]>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:15])[CH:6]=[C:5]2[CH3:11]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 223515035-Fluoro-3-methyl-1H-indole

Product 1

HCID 187296765-Fluoro-1,3-dimethyl-1H-indoleYield 78.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-fluoro-3-methyl-indole (CAS: 392-13-2, 2.5 g) in DMF (20 ml) was added potassium hydroxide (1.41 g). The suspension was stirred at rt for 1 h and iodomethane (2.85 g) was added dropwise at 0-5° C. The reaction mixture was stirred at rt for 18 h and concentrated under high vacuum. The residue was quenched with water and extracted with ethyl acetate. The organics were washed, dried and concentrated. The crude residue was chromatographed on silica gel using heptane/ethyl acetate as eluent to obtain the desired compound (2.15 g) as a colorless liquid. MS (EI): 163.1 (M)

Workup

  1. stirringThe reaction mixture was stirred at rt for 18 h
  2. concentrationconcentrated under high vacuum
  3. customThe residue was quenched with water
  4. extractionextracted with ethyl acetate
  5. washThe organics were washed
  6. customdried
  7. concentrationconcentrated
  8. customThe crude residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-fe867d1c5709445e8feefb28b0b4905f
Source dataset
uspto-grants-2012_04
Patent number
US08158655B2

Reaction notes

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