Ethyl 7-[cyclopropyl(pyridin-2-ylsulfonyl)amino]-5-(2-methoxyethoxy)indoline-2-carboxylate → ethyl 7-[cyclopropyl(pyridin-2-ylsulfonyl)amino]-5-(2-methoxyethoxy)-1H-indole-2-carboxylate

HRID 1960446Notes

Reaction equation

HRID 1960446 reaction equation
[CH:1]1([N:4]([S:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=2)(=[O:26])=[O:25])[C:5]2[CH:6]=[C:7]([O:19][CH2:20][CH2:21][O:22][CH3:23])[CH:8]=[C:9]3[C:13]=2[NH:12][CH:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:10]3)[CH2:3][CH2:2]1>[O-2].[Mn+4].[O-2].C1(C)C=CC=CC=1>[CH:1]1([N:4]([S:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=2)(=[O:26])=[O:25])[C:5]2[CH:6]=[C:7]([O:19][CH2:20][CH2:21][O:22][CH3:23])[CH:8]=[C:9]3[C:13]=2[NH:12][C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:10]3)[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 59136057Ethyl 7-[cyclopropyl(pyridin-2-ylsulfonyl)amino]-5-(2-methoxyethoxy)indoline-2-carboxylate

Product 1

HCID 57476255ethyl 7-[cyclopropyl(pyridin-2-ylsulfonyl)amino]-5-(2-methoxyethoxy)-1H-indole-2-carboxylateYield 94.3%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent

Procedure

To a mixture of ethyl 7-[cyclopropyl(pyridin-2-ylsulfonyl)amino]-5-(2-methoxyethoxy)indoline-2-carboxylate (1.31 g) and toluene (30 mL) was added manganese (IV) oxide (0.99 g) at room temperature, and the mixture was refluxed for 3 hr. The catalyst was filtered off, and the filtrate was concentrated. The residue was subjected to silica gel column chromatography to give the title compound (1.23 g, yield 94%) as a colorless solid from a fraction eluted with ethyl acetate-hexane (4:1, volume ratio).

Workup

  1. temperaturethe mixture was refluxed for 3 hr
  2. filtrationThe catalyst was filtered off
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-a6088fe74171453b96e3cda1b8d6dc1e
Source dataset
uspto-grants-2013_04
Patent number
US08410087B2

Reaction notes

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