3-Benzenesulfonyl-5-chloroindole-2-carboxamide → 5-chloro-3-(phenylsulfonyl)-1H-Indole-2-carbonitrile

HRID 260494Notes

Reaction equation

HRID 260494 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([NH2:13])=O)=[C:5]2[S:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:16])=[O:15].[OH-].CCC[N+](S(=O)(=O)NC(O)=O)(CC)CC>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]#[N:13])=[C:5]2[S:14]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)(=[O:16])=[O:15]

Participants

4

Reactant 2

HCID 4548443-Benzenesulfonyl-5-chloroindole-2-carboxamideHCID 86749577Methyl (carboxysulfamoyl)triethylammonium hydroxide

Product 1

HCID 224015145-chloro-3-(phenylsulfonyl)-1H-Indole-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Chloro-3-phenylsulfonylindole-2-carboxamide reacts with methyl (carboxysulfamoyl)triethylammonium hydroxide inner salt (Burgess reagent) in tetrahydrofuran (THF) solvent as described by D. A. Claremon and B. T. Phillips (Tetrahedron Lett., 29, 2155 (1988)) to provide the title compound.

Sources & evidence

ORD record
ord-0b1fe20c76aa419b99e691b77546a0e6
Source dataset
uspto-grants-1996_06
Patent number
US05527819

Reaction notes

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