Hydrochloric Acid → N-Tosylindole

HRID 2042940Notes

Reaction equation

HRID 2042940 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].[S:12](Cl)([C:15]1[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=1)(=[O:14])=[O:13].Cl>CN(C=O)C>[S:12]([N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[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 313Hydrochloric AcidHCID 798IndoleHCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydride

Product 1

HCID 10956616N-TosylindoleYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of indole 81 (10 g, 85 mmol) in DMF (50 mL) at 0° C. was added NaH (60% dispersion in mineral oil 4 g) and tosylchloride (24 g, 128 mmol) portionwisely. And the reaction mixture was stirred at room temperature for 2 h. The resulting solution was acidified with 2.0 M HCl, and organic layer was extracted with Et2O. After evaporating the volatile material with reduced pressure, the residue was purified by silica column chromatography to obtain titled compound 82 (19 g, 84%).

Workup

  1. extractionwas extracted with Et2O
  2. customAfter evaporating the volatile material with reduced pressure
  3. customthe residue was purified by silica column chromatography

Sources & evidence

ORD record
ord-4f5fb899a43c4bef9347386cee446600
Source dataset
uspto-grants-2013_11
Patent number
US08586550B2

Reaction notes

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