4-Toluenesulfonyl chloride → 1-(4-Methylbenzene-1-sulfonyl)-1H-indole-3-carbaldehyde

HRID 1854672Notes

Reaction equation

HRID 1854672 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]=[O:11])=[CH:2]1.[H-].[Na+].[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1>CS(C)=O.C(OCC)(=O)C.[NH4+].[Cl-]>[S:20]([N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]=[O:11])=[CH:2]1)([C:17]1[CH:18]=[CH:19][C:14]([CH3:24])=[CH:15][CH:16]=1)(=[O:22])=[O:21]

Participants

7

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 10256Indole-3-CarboxaldehydeHCID 24758Sodium hydride

Product 1

HCID 7358171-(4-Methylbenzene-1-sulfonyl)-1H-indole-3-carbaldehydeYield 50%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a solution of 1H-indole-3-carboxaldehyde (300 mg, 2.07 mmol) in 6.2 mL of dry dimethylsulfoxide was added sodium hydride (108 mg, 55%, 2.5 mmol) under nitrogen at 0° C. After the reaction mixture was stirred for 30 min at room temperature, p-toluenesulfonyl chloride (434 mg, 2.28 mmol) was added with additional stirring for 1 h. The reaction mixture was diluted with 10 mL of ethyl acetate and 10 mL of saturated NH4Cl aqueous solution, successively, and the solution was extracted with 100 mL of ethyl acetate. The extract was washed with saturated NaHCO3 aqueous solution, brine, and dried over MgSO4 After filtration, the solution was concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20 to 60/40) to obtain the title compound as a pale yellow solid (310 mg, 50%).

Workup

  1. stirringwith additional stirring for 1 h
  2. extractionsuccessively, and the solution was extracted with 100 mL of ethyl acetate
  3. washThe extract was washed with saturated NaHCO3 aqueous solution, brine
  4. dry with materialdried over MgSO4
  5. filtrationAfter filtration
  6. concentrationthe solution was concentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20 to 60/40)

Sources & evidence

ORD record
ord-fc845f6c0b2944f9a49e76f679e71289
Source dataset
uspto-grants-2015_02
Patent number
US08962674B2

Reaction notes

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