80360-26-5

Usage

Chemical class

Indole derivatives

Characteristic features

Two iodine atoms, a phenylsulfonyl group attached to the indole ring

Potential applications

Organic chemistry, pharmaceuticals

Unique attributes

Structural features, reactivity

Usage

Building block for synthesis of organic molecules, possible biological activity

Relevance

Interest for drug discovery and development, valuable tool for chemical research and synthesis processes

Upstream product

• 40899-71-6 1-benzenesulfonylindole 
• 192991-41-6 1-(phenylsulfonyl)indole-2,3-dicarboxylic acid 
• 120-72-9 indole 
• 26340-47-6 3-Iodo-1H-indole 
• 80360-14-1 3-iodo-1-phenylsulfonyl-1H-indole 
• 80360-25-4 1-(phenylsulfonyl)-2-lithio-3-iodoindole 
• 139409-35-1 2,3-diiodo-1H-indole 
• 98-09-9 benzenesulfonyl chloride 

Downstream Products

• 84416-65-9 ethyl 2-(N-carboethoxyphenylsulfonamido)phenylpropiolate 
• 321896-79-1 2,3-bis(4-methoxyphenyl)-1-(phenylsulfonyl)indole 
• 403642-46-6 (1-benzenesulfonyl-3-iodo-1H-indol-2-yl)-furan-2-yl-methanone 
• 692259-48-6 3-(1-benzenesulfonyl-3-iodo-1H-indol-2-yl)-cyclohex-2-enone 
• 403642-45-5 (1-benzenesulfonyl-3-iodo-1H-indol-2-yl)-phenyl-methanone 
• 857934-94-2 3-iodo-1-(phenylsulfonyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole 
• 84416-64-8 2-(phenylsulfonamido)phenyl-acetylene 
• 80360-17-4 1-(phenylsulfonyl)-3-(trimethylsilyl)indole 
• 84416-66-0 <2-(phenylsulfonamido)phenyl>trimethylsilylacetylene 
• 84416-68-2 1-Benzenesulfonyl-2,3-bis-trimethylsilanyl-1H-indole 
• 3469-20-3 2,3-diphenyl-1H-indole 
• 5034-76-4 indoxole 

Relevant academic research and scientific papers

Decarboxylative halogenation of indolecarboxylic acids using hypervalent iodine(III) reagent and its application to the synthesis of polybromoindoles

Hypervalent iodine mediated decarboxylative halogenation of indoledicarboxylic acid derivatives was studied. The treatment of 1-methylindole-2,3-dicarboxylic acid with phenyliodine diacetate (PIDA) in the presence of lithium bromide gave 1-methyl-3,3-brom

A convenient iodination of indoles and derivatives

We report a direct iodination of indole and derivative compounds with iodine monochloride (ICl) in the presence of Celite. This procedure has now been extended to the iodination of substituted indoles, azaindoles and pyrroles. The scope of this procedure

Hypervalent iodine(III) mediated decarboxylative halogenation of indolecarboxylic acids for the synthesis of haloindole derivatives

The treatment of 1-methylindole-2,3-dicarboxylic acid with hypervalent iodine(III) reagent, phenyliodine diacetate (PIDA), in the presence of lithium bromide gave 1-methyl-3,3-dibromooxindole. However, the reaction of 1-(phenylsulfonyl)indole-2,3-dicarboxylic acid with PIDA in the presence of lithium bromide afforded 2,3-dibromo-1-(phenylsulfonyl)indole. In a similar manner, the 2,3-dichloro- and 2,3-diiodo-indole derivatives were obtained by the reaction of the indole-2,3-dicarboxylic acids with PIDA in the presence of lithium chloride and iodide. Georg Thieme Verlag Stuttgart New York.

Bis-Suzuki reactions of 2,3-dihaloindoles. A convenient synthesis of 2,3-diarylindoles

A convenient, one-pot synthesis of 2,3-diarylindoles 4 is described via a bis-Suzuki palladium-catalyzed cross coupling of 2,3-dihalo-1-(phenylsulfonyl)indoles 1 with arylboronic acids 2, followed by cleavage of the N-protecting group to give 4. The anti-inflammatory drug indoxole (4c) is prepared in high yield. (C) 2000 Elsevier Science Ltd.

Generation and Reactions of 3-Lithio-1-(phenylsulfonyl)indole

Treatment of 1-(phenylsulfonyl)-3-iodoindole (6) with 2 equiv of tert-butyllithium (-100 deg C THF) generates essentially quantitatively 3-lithio-1-(phenylsulfonyl)indole (1).Quenching 1 with various electrophiles gives 3-substituted indoles in good yield