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

HRID 1749771Notes

Reaction equation

HRID 1749771 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.[S:12](Cl)([C:15]1[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=1)(=[O:14])=[O:13].C(N(C(C)C)CC)(C)C.C(=O)([O-])O.[Na+]>C(Cl)Cl>[S:12]([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:15]1[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=1)(=[O:14])=[O:13]

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 10256Indole-3-CarboxaldehydeHCID 81531DiisopropylethylamineHCID 516892Sodium Bicarbonate

Product 1

HCID 7358171-(4-Methylbenzene-1-sulfonyl)-1H-indole-3-carbaldehydeYield 78.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1H-indole-3-carboxaldehyde (7.26 g, 50.0 mmol) in methylene chloride (100 mL) was added with tosyl chloride (11.4 g, 60.0 mmol) and diisopropylethylamine (7.75 g, 60.0 mmol), and the mixture was stirred overnight at room temperature. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate to terminate the reaction, and then extracted three times with methylene chloride, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain 1-tosyl-1H-indole-3-carboxaldehyde (11.8 g, 78%).

Workup

  1. customto terminate
  2. customthe reaction
  3. extractionextracted three times with methylene chloride
  4. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-09dc648d0c1a4ccba94c4976255b2efd
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

Loading…