N-Methylaniline → HCID 67731710, compound

HRID 260486Notes

Reaction equation

HRID 260486 reaction equation
[CH3:1]NC1C=CC=CC=1.[C:9]([C:14]1[N:15]([S:28]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)(=[O:30])=[O:29])[C:16]2[C:21]([C:22]=1S(Cl)(=O)=O)=[CH:20][C:19]([Cl:27])=[CH:18][CH:17]=2)([O:11][CH2:12][CH3:13])=[O:10]>>[C:9]([C:14]1[N:15]([S:28]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)(=[O:29])=[O:30])[C:16]2[C:21]([CH:22]=1)=[CH:20][C:19]([Cl:27])=[CH:18][CH:17]=2)([O:11][CH2:12][CH3:13])=[O:10].[CH3:1][C:35]1[CH:36]=[C:31]([S:28]([NH2:15])(=[O:29])=[O:30])[CH:32]=[CH:33][CH:34]=1

Participants

3

Reactant 2

HCID 7515N-MethylanilineHCID 22401482ethyl 5-chloro-3-(chlorosulfonyl)-1-(phenylsulfonyl)-1H-indole-2-carboxylate

Product 1

HCID 67731710HCID 67731710, compound

Procedure

In the manner outlined in Example 68, Step B, N-methylaniline was added to 2-carboethoxy-5-chloro-1-phenylsulfonylindole-3-sulfonylchloride to give, after flash column chromatography on silica (dry loaded, eluting with an ethyl acetate/hexanes gradient, 10-30% ethyl acetate) the title compound as colorless crystals (from dichloromethane/hexanes);

Workup

  1. customto give
  2. customafter flash column chromatography on silica (dry
  3. washeluting with an ethyl acetate/hexanes gradient, 10-30% ethyl acetate) the title compound as colorless crystals (from dichloromethane/hexanes)

Sources & evidence

ORD record
ord-b23f0e8fe6554bb98ab42c151db49e28
Source dataset
uspto-grants-1996_06
Patent number
US05527819

Reaction notes

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