5-Iodoisatin → HCID 178517201, compound

HRID 642089Notes

Reaction equation

HRID 642089 reaction equation
[I:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=O.[NH:13]([C:15]([C:17]1[CH:38]=[CH:37][C:20]([C:21]([NH:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([S:30]([C:33]([F:36])([F:35])[F:34])(=[O:32])=[O:31])[CH:25]=2)=[O:22])=[CH:19][CH:18]=1)=[O:16])[NH2:14]>C(O)(=O)C>[I:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[N:14][NH:13][C:15]([C:17]1[CH:38]=[CH:37][C:20]([C:21]([NH:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([S:30]([C:33]([F:34])([F:35])[F:36])(=[O:31])=[O:32])[CH:25]=2)=[O:22])=[CH:19][CH:18]=1)=[O:16]

Participants

4

Reactant 2

HCID 886955-IodoisatinHCID 10134790HCID 10134790, compound

Product 1

HCID 178517201HCID 178517201, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

Into a suspension of 5-iodo-1H-indole-2,3-dione in acetic acid was added 4-(hydrazinocarbonyl)-N-{3-[(trifluoromethyl)sulfonyl]phenyl}benzamide. After stirring at 100° C., the reaction mixture was cooled to rt and a yellow solid precipitated out. Filtration on a fritté, washing with AcOH, water and drying under vacuo at 60° C. overnight gave 80 mg of the title compound (76%) as a yellow solid in 76% purity by HPLC (Rt: 4.96, gradient of 8 min, MaxPlot detection between 230 and 400 nm).

Workup

  1. temperaturethe reaction mixture was cooled to rt
  2. customa yellow solid precipitated out
  3. filtrationFiltration on a fritté
  4. washwashing with AcOH, water
  5. customdrying under vacuo at 60° C. overnight

Sources & evidence

ORD record
ord-df3fc10747a94daca0b57ddb864c6324
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Reaction notes

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