4-Toluenesulfonyl chloride → 1-Tosyl-1H-indole-4-carbaldehyde

HRID 475182Notes

Reaction equation

HRID 475182 reaction equation
[NH:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([CH:10]=[O:11])[C:4]=2[CH:3]=[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>C1COCC1>[S:20]([N:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([CH:10]=[O:11])[C:4]=2[CH:3]=[CH:2]1)([C:17]1[CH:18]=[CH:19][C:14]([CH3:24])=[CH:15][CH:16]=1)(=[O:22])=[O:21]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 333703Indole-4-carboxaldehyde

Product 1

HCID 131150931-Tosyl-1H-indole-4-carbaldehydeYield 15%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1H-indole-4-carbaldehyde (2.9 g, 20 mmol) in THF (50 mL) cooled in an ice bath was added NaH (0.96 g, 60% in oil, 24 mmol) with vigorous stirring. After stirring for 30 min, 4-toluenesulfonyl chloride (5.73 g, 30 mmol) was added. The mixture was stirred at RT overnight and the solvent was removed in vacuo. The residue was diluted with DCM (500 mL) and water (50 mL). The organic layer was separated, dried (MgSO4), filtered and concentrated. The crude product was purified by SiO2 chromatography eluting with a petroleum ether/EtOAc gradient (5 to 10% EtOAc) to afford 900 mg (15%) of 1-tosyl-1H-indole-4-carbaldehyde (42) as white solid: MS (ESI) m/z=300.1 [M+1]+.

Workup

  1. stirringThe mixture was stirred at RT overnight
  2. customthe solvent was removed in vacuo
  3. additionThe residue was diluted with DCM (500 mL) and water (50 mL)
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by SiO2 chromatography
  9. washeluting with a petroleum ether/EtOAc gradient (5 to 10% EtOAc)

Sources & evidence

ORD record
ord-af93e4fd96a242f988ffd8491f5a65e4
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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