Pyridine → 5-(2,3-Dihydro-indole-1-sulfonyl)-1,3-dihydro-indol-2-one

HRID 991818Notes

Reaction equation

HRID 991818 reaction equation
Cl[S:2]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[CH2:8]2)(=[O:4])=[O:3].[NH:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:17][CH2:16]1.N1C=CC=CC=1>C1COCC1>[N:15]1([S:2]([C:5]2[CH:6]=[C:7]3[C:11](=[CH:12][CH:13]=2)[NH:10][C:9](=[O:14])[CH2:8]3)(=[O:4])=[O:3])[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 10328IndolineHCID 49625062-oxo-2,3-dihydro-1H-indole-5-sulfonyl chloride

Product 1

HCID 76674175-(2,3-Dihydro-indole-1-sulfonyl)-1,3-dihydro-indol-2-oneYield 110.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 5-chlorosulfonyl-2-oxindole (5 g, 21.6 mmol) and indoline (2.9 mL, 26 mmol) in THF (20 mL) was added pyridine (3.4 g, 43 mmol). After stirring at room temperature for one day, the precipitate was collected by filtration, washed with water in ethanol (20%), dried, washed with 60 mL of hot ethanol and dried under vacuum to give 7.5 g (over 100%) of 5-(2,3-dihydro-indole-1-sulfonyl)-1,3-dihydro-indol-2-one as a pink solid.

Workup

  1. filtrationthe precipitate was collected by filtration
  2. washwashed with water in ethanol (20%)
  3. customdried
  4. washwashed with 60 mL of hot ethanol
  5. customdried under vacuum

Sources & evidence

ORD record
ord-ac38ce781802475c80728f9b37471584
Source dataset
uspto-grants-2002_10
Patent number
US06465507B2

Reaction notes

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