4-Toluenesulfonyl chloride → HCID 13720819, compound

HRID 878939Notes

Reaction equation

HRID 878939 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]([O:12][CH3:13])=[O:11])[CH:8]=2)[CH:3]=[CH:2]1.C(=O)([O-])[O-].[K+].[K+].[CH3:20][C:21]1[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1>CC(=O)CCC>[S:27]([N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]([O:12][CH3:13])=[O:11])[CH:8]=2)[CH:3]=[CH:2]1)([C:24]1[CH:25]=[CH:26][C:21]([CH3:20])=[CH:22][CH:23]=1)(=[O:29])=[O:28]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 11430Potassium CarbonateHCID 639844Methyl indole-6-carboxylate

Product 1

HCID 13720819HCID 13720819, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 78952-PentanoneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of methyl indole-6-carboxylate (2.1 g) of 2-pentanone (40 mL), potassium carbonate (6.5 g) and 4-methylbenzenesulfonyl chloride (4.4 g) were added at room temperature, and then the reaction mixture was stirred at 80° C. for 16 hours. After cooling to room temperature, the insoluble materials were filtered, and the filtrate was concentrated under reduced pressure. To the obtained residue, a mixed solvent of ethyl acetate-hexane was added, and the obtained solid was filtered, and washed with hexane to give the titled compound (3.6 g) as a white solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe insoluble materials were filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionTo the obtained residue, a mixed solvent of ethyl acetate-hexane was added
  5. filtrationthe obtained solid was filtered
  6. washwashed with hexane

Sources & evidence

ORD record
ord-c642b472c78f4c49a27b1e74e649c34d
Source dataset
uspto-grants-2015_03
Patent number
US08987473B2

Reaction notes

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