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

HRID 1372430Notes

Reaction equation

HRID 1372430 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>O1CCCC1>[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 tetrahydrofuran (20 mL) was added pyridine (3.4 g, 43 mmol). After stirring at room temperature for 1 day the precipitate was collected by vacuum filtration, washed with water in ethanol (20%), dried, washed with 60 mL of hot ethanol and dried under vacuum to give 7.5 g of 5-(2,3-dihydro-indole-1-sulfonyl)-1,3-dihydro-indol-2-one as a pink solid. 1H-NMR (360 MHz, dimethylsulfoxide-d6) δ 10.76 (br s, 1H, NH), 7.62 (m, 2H), 7.43 (d, 1H), 7.13–7.18 (m, 2H), 6.95 (dt, 1H), 6.90 (d, 1H), 3.87 (t, 2H, CH2), 3.51 (s, 2H, CH2), 2.91 (t, 2H, CH2). MS m/z 315 [M+1].

Workup

  1. filtrationwas collected by vacuum 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-df035b7426d74bcbb69c50f858f5ce3a
Source dataset
uspto-grants-2007_01
Patent number
US07157577B2

Reaction notes

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