91579-92-9

Basic information

• Product Name: 1H-Pyrrole, 3-(chloroacetyl)-1-(phenylsulfonyl)-
• Synonyms: 1H-Pyrrole,3-(chloroacetyl)-1-(phenylsulfonyl);1-phenylsulphonyl-3-chloroacetyl-pyrrole;1-phenylsulfonyl-3-chloroacetylpyrrole;2-chloro-1-(1-(phenylsulfonyl)-1H-pyrrol-3-yl)ethanone
• CAS NO: 91579-92-9
• Molecular Formula: C12H10ClNO3S
• Molecular Weight: 283.73100
• Mol File: 91579-92-9.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 1H-Pyrrole, 3-(chloroacetyl)-1-(phenylsulfonyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrrole, 3-(chloroacetyl)-1-(phenylsulfonyl)-(91579-92-9)
• EPA Substance Registry System: 1H-Pyrrole, 3-(chloroacetyl)-1-(phenylsulfonyl)-(91579-92-9)

Safety Data

• Hazardous Substances Data: 91579-92-9(Hazardous Substances Data)

Upstream product

• 81453-98-7 3-acetyl-1-(phenylsulfonyl)pyrrole 
• 16851-82-4 N-phenylsulfonylpyrrole 
• 79-04-9 chloroacetyl chloride 

Downstream Products

• 109482-63-5 1-(1-Benzenesulfonyl-1H-pyrrol-3-yl)-2-iodo-ethanone 
• 91579-98-5 1-(1-phenylsulfonylpyrrol-3-yl)-2-chloroethanol 
• 91580-03-9 1-phenylsulphonyl-3-azidoacetyl-pyrrole 
• 1421517-98-7 N1--benzenesulfonyl-4--methoxy--6--azainole N6-oxide 
• 1421517-89-6 N1--benzenesulfonyl-7--bromo-4--methoxy--6--azainole 
• 1421517-99-8 N1--benzenesulfonyl-4-methoxy-6--azainole 
• 1449413-23-3 1-(4-benzoylpiperazin-1-yl)-2-(7-bromo-4-methoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)ethane-1,2-dione 
• 122450-26-4 (S)-2-[Bis-((S)-sec-butyl)-amino]-1-[1-(2-chloro-benzyl)-1H-pyrrol-3-yl]-ethanol 
• 122450-26-4 (R)-2-[Bis-((S)-sec-butyl)-amino]-1-[1-(2-chloro-benzyl)-1H-pyrrol-3-yl]-ethanol 
• 122450-33-3 2-[Bis-((S)-sec-butyl)-amino]-1-[1-(2-chloro-benzyl)-1H-pyrrol-3-yl]-ethanone 
• 122450-32-2 2-[Bis-((R)-sec-butyl)-amino]-1-[1-(2-chloro-benzyl)-1H-pyrrol-3-yl]-ethanone 
• 122450-31-1 1-[1-(2-Chloro-benzyl)-1H-pyrrol-3-yl]-2-iodo-ethanone 
• 122450-27-5 1-o-chlorobenzyl-3-chloroacetylpyrrole 
• 91580-04-0 1-(1-phenylsulphonylpyrrol-3-yl)-2-azido-ethanol 

Relevant articles and documents

Preparation of the HIV Attachment Inhibitor BMS-663068. Part 3. Mechanistic Studies Enable a Scale-Independent Friedel-Crafts Acylation

During the development of a Friedel-Crafts acylation for the preparation of a key pyrrole intermediate in the synthesis of the HIV attachment inhibitor, BMS-663068-03, a significant scale dependence was found. A precipitous drop in yield was observed for

Synthesis of the 6-azaindole containing HIV-1 attachment inhibitor pro-drug, BMS-663068

The development of a short and efficient synthesis of a complex 6-azaindole, BMS-663068, is described. Construction of the 6-azaindole core is quickly accomplished starting from a simple pyrrole, via a regioselective Friedel.Crafts acylation, Pictet.Spengler cyclization, and a radical-mediated aromatization. The synthesis leverages an unusual heterocyclic Noxide α-bromination to functionalize a critical C.H bond, enabling a highly regioselective copper-mediated Ullmann. Goldberg.Buchwald coupling to install a challenging triazole substituent. This strategy resulted in an efficient 11 step linear synthesis of this complex clinical candidate.