91579-92-9

Upstream product

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

Downstream Products

• 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 
• 91579-99-6 1-(1-phenylsulfonylpyrrol-3-yl)-2-isopropylamino-ethanol 
• 91580-01-7 1-(1-Benzenesulfonyl-1H-pyrrol-3-yl)-2-isopropylamino-ethanone 
• 91580-02-8 1-(1-phenylsulfonylpyrrol-3-yl)-2-methylamino-ethanol 

Relevant academic research and scientific papers

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.

Palauchlor: A practical and reactive chlorinating reagent

Unlike its other halogen atom siblings, the utility of chlorinated arenes and (hetero)arenes are twofold: they are useful in tuning electronic structure as well as acting as points for diversification via cross-coupling. Herein we report the invention of a new guanidine-based chlorinating reagent, CBMG or "Palauchlor", inspired by a key chlorospirocyclization en route to pyrrole imidazole alkaloids. This direct, mild, operationally simple, and safe chlorinating method is compatible with a range of nitrogen-containing heterocycles as well as select classes of arenes, conjugated π-systems, sulfonamides, and silyl enol ethers. Comparisons with other known chlorinating reagents revealed CBMG to be the premier reagent.