158991-81-2

Basic information

• Product Name: 6-bromo-N-(1-p-toluenesulphonyl)-indole-3-carboxaldehyde
• Synonyms: 6-bromo-N-(1-p-toluenesulphonyl)-indole-3-carboxaldehyde
• CAS NO: 158991-81-2
• Molecular Weight: 378.246
• Mol File: 158991-81-2.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 6-bromo-N-(1-p-toluenesulphonyl)-indole-3-carboxaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 6-bromo-N-(1-p-toluenesulphonyl)-indole-3-carboxaldehyde(158991-81-2)
• EPA Substance Registry System: 6-bromo-N-(1-p-toluenesulphonyl)-indole-3-carboxaldehyde(158991-81-2)

Safety Data

• Hazardous Substances Data: 158991-81-2(Hazardous Substances Data)

Upstream product

• 17826-04-9 6-bromo-1H-indole-3-carbaldehyde 
• 52415-29-9 6-bromo-1H-indole 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 1417616-19-3 (S)-2-((R)-1-(6-bromo-1-tosyl-1H-indol-3-yl)-2-nitroethyl)-pentanal 
• 1417616-20-6 (2S,3R)-3-(6-bromo-1-tosyl-1H-indol-3-yl)-2-isopropyl-4-nitrobutanal 
• 1417616-21-7 (S)-2-((R)-1-(6-bromo-1-tosyl-1H-indol-3-yl)-2-nitroethyl)-heptanal 
• 1417616-23-9 (S)-2-((R)-1-(6-bromo-1-tosyl-1H-indol-3-yl)-2-nitroethyl)octanal 
• 1417616-27-3 (2S,3R)-3-(6-bromo-1-tosyl-1H-indol-3-yl)-2-ethyl-4-nitrobutan-1-ol 
• 1417616-02-4 (E)-6-bromo-3-(2-nitrovinyl)-1-tosyl-1H-indole 
• 158991-88-9 6-bromo-3-(2'-imino-5'-oxo-4'-imidazolinylidenemethyl)-1-(p-toluenesulphonyl)-1H-indole 
• 354538-23-1 (R)-6-bromo-N-[(N-tosyl-6-bromoindol-3-yl)azidoethyl]-α-oxoindole-3-acetamide 
• 354538-37-7 (R)-3-(6-bromoindol-3-yl)-6-(N-tosyl-6-bromoindol-3-yl)-5,6-dihydro-2(1H)-pyrazinone 
• 354538-35-5 (1R)-N-(tert-butyloxycarbonyl)-1-(N-tosyl-6-bromoindol-3-yl)-2-[(4-methylphenylsulfonyl)oxy]ethylamine 
• 354538-36-6 (1R)-N-(tert-butyloxycarbonyl)-1-(N-tosyl-6-bromoindol-3-yl)-2-azidoethylamine 
• 354538-32-2 (1R)-1-(N-tosyl-6-bromoindol-3-yl)-1-azido-2-[(tert-butyldimethylsilyl)oxy]ethane 
• 354538-30-0 (1S)-1-(N-tosyl-6-bromoindol-3-yl)-2-[(tert-butyldimethylsilyl)oxy]-1-ethanol 
• 354538-34-4 (R)-2-azido-2-(N-tosyl-6-bromoindol-3-yl)-1-ethanol 

Relevant articles and documents

Unusual Formation of Cyclopenta[ b]indoles from 3-Indolylmethanols and Alkynes

Acid-promoted synthesis of cyclopenta[b]indole frameworks from 3-indolylmethanols and alkynes has been reported. The overall transformation represents a formal [3 + 2] annulation via rearrangement. This protocol showed good generality for the carbinol substrates as well as alkynes and allowed the generation of structurally diverse cyclopenta[b]indoles. Terminal alkynes, dialkyl-substituted internal alkynes, and alkynes with electron-deficient substituents were found to be not suitable for this transformation. Similarly, N-Ts and N-Boc groups were compatible with reaction conditions, whereas N-Ac and N-Tf failed to undergo this reaction. Isolation of vinyl chloride intermediate suggested the involvement of a vinylic carbocation intermediate. A mechanism has been proposed involving a ring-opening-ring-closing cascade followed by a 1,3-indole migration process via a spirocyclobutene intermediate.

Enantioselective synthesis for the (-)-antipode of the pyrazinone marine alkaloid, hamacanthin A

A short enantioselective total synthesis for the (-)-antipode of the antifungal marine alkaloid, hamacanthin A, (6R)-3,6-bis(6-bromoindol-3-yl)-5,6-dihydro-2(1H)-pyrazinone, is described. This synthesis proceeds through the coupling of 3-indolyl-αoxoacetyl chloride and 3-indolyl azidoethylamine, followed by intramolecular aza-Wittig type cyclization. A concise and useful approach for the synthesis of (1R)-1-(indol-3-yl)-2-azidoethylamine using the Sharpless asymmetric dihydroxylation reaction followed by stereospecific azidation is also presented.