p-Toluenesulfonic acid → methyl 4-fluoro-1H-indole-2-carboxylate

HRID 1249930Notes

Reaction equation

HRID 1249930 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:11]([OH:13])=[O:12])[NH:6]2.[C:14]1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH3:14][O:12][C:11]([C:5]1[NH:6][C:7]2[C:3]([CH:4]=1)=[C:2]([F:1])[CH:10]=[CH:9][CH:8]=2)=[O:13]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 40355794-Fluoroindole-2-carboxylic acid

Product 1

HCID 4715435methyl 4-fluoro-1H-indole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

25 4-Fluoroindole-2-carboxylic acid (0.65 g, 3.40 mmol) was dissolved in methanol (50 ml), and 4-toluenesulfonic acid (1.4 g, 7.36 mmol) was added under nitrogen. The solution was stirred at reflux for 24 hours. Most of the methanol was removed by evaporation, and the residue was dissolved in dicholoromethane (100 ml), washed with saturated sodium carbonate, and the organic layer was separated. The aqueous layer was extracted with dichloromethane (3×50 ml). The combined organic layers were washed with water, dried over sodium sulphate, and evaporated to yield a yellow crystalline material.

Workup

  1. temperatureat reflux for 24 hours
  2. customMost of the methanol was removed by evaporation
  3. dissolutionthe residue was dissolved in dicholoromethane (100 ml)
  4. washwashed with saturated sodium carbonate
  5. customthe organic layer was separated
  6. extractionThe aqueous layer was extracted with dichloromethane (3×50 ml)
  7. washThe combined organic layers were washed with water
  8. dry with materialdried over sodium sulphate
  9. customevaporated
  10. customto yield a yellow crystalline material

Sources & evidence

ORD record
ord-cbb023b3e5634a33a8436dc7d39aef61
Source dataset
uspto-grants-2002_01
Patent number
US06335360B1

Reaction notes

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