Water → 1-(4-Methylbenzene-1-sulfonyl)-1H-indole-5-carbonitrile

HRID 1166733Notes

Reaction equation

HRID 1166733 reaction equation
[H-].[Na+].[C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][CH:9]=[CH:8]2)#[N:4].[S:14](Cl)([C:17]1[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=1)(=[O:16])=[O:15].O>C1COCC1>[C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([S:14]([C:17]1[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=1)(=[O:16])=[O:15])[CH:9]=[CH:8]2)#[N:4]

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 27513Indole-5-carbonitrile

Product 1

HCID 224925731-(4-Methylbenzene-1-sulfonyl)-1H-indole-5-carbonitrileYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In a 100 mL round-bottom flask was placed NaH (0.4 g, 60% dipersion in mineral oil, 10 mmol) and anhydrous THF (10 mL) was added. To the suspension was added a solution of 5-cyanoindole (1.0 g, 7 mmol) in anhydrous THF (10 mL) by syringe at 0° C. The mixture was stirred for 10 min, and tosyl chloride (1.6 g, 8.4 mmol) was added. After stirring at room temperature for 2 h, water (100 mL) was added. The mixture was extracted with ethyl acetate (3×50 mL), dried (MgSO4), and concentrated. The residue was purified by column chromatography using hexane: ethyl acetate=2:1 as eluent to yield 1.86 g (92%) of the desired product.

Workup

  1. customIn a 100 mL round-bottom flask was placed
  2. stirringAfter stirring at room temperature for 2 h
  3. extractionThe mixture was extracted with ethyl acetate (3×50 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-e2a46901e31843dfb936835594f25842
Source dataset
uspto-grants-2003_09
Patent number
US06613942B1

Reaction notes

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