1421517-89-6

Basic information

• Product Name: N1--benzenesulfonyl-7--bromo-4--methoxy--6--azainole
• Synonyms: N1--benzenesulfonyl-7--bromo-4--methoxy--6--azainole
• CAS NO: 1421517-89-6
• Molecular Weight: 367.223
• Mol File: 1421517-89-6.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: N1--benzenesulfonyl-7--bromo-4--methoxy--6--azainole(CAS DataBase Reference)
• NIST Chemistry Reference: N1--benzenesulfonyl-7--bromo-4--methoxy--6--azainole(1421517-89-6)
• EPA Substance Registry System: N1--benzenesulfonyl-7--bromo-4--methoxy--6--azainole(1421517-89-6)

Safety Data

• Hazardous Substances Data: 1421517-89-6(Hazardous Substances Data)

Upstream product

• 16851-82-4 N-phenylsulfonylpyrrole 
• 91579-92-9 2-chloro-1-(1-(phenylsulfonyl)-1H-pyrrol-3-yl)ethanone 
• 1421517-98-7 N1--benzenesulfonyl-4--methoxy--6--azainole N6-oxide 
• 357263-40-2 4-methoxy-6-azaindole 
• 98-09-9 benzenesulfonyl chloride 
• 1421517-99-8 N1--benzenesulfonyl-4-methoxy-6--azainole 

Downstream Products

• 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 

Relevant articles and documents

Preparation of the HIV Attachment Inhibitor BMS-663068. Part 5. Selective C-7 Bromination of the 6-Azaindole Core

We report research focused on the preparation of an advanced intermediate in the synthesis of a novel antiretroviral. This manuscript describes the development of an efficient oxidation of a 6-azaindole derivative, the bromination of the resulting N-oxide using PyBroP, the removal of the protecting group, and the isolation of the brominated azaindole product. The work reported herein has been successfully implemented in the multikilogram scale to fund development and clinical activities of BMS-663068.

A PROCESS FOR PREPARING HALOGENATED AZAINDOLE COMPOUNDS USING PYBROP

A process for preparing halogenated azaindole compounds makes use of a brominating agent PyBroP, together with a dehydrating agent BSA to enhance the selectivity and improve the yield of the final product which is a piperazine prodrug useful as an antiviral.

Regioselective bromination of fused heterocyclic N-oxides

A mild method for the regioselective C2-bromination of fused azine N-oxides is presented, employing tosic anhydride as the activator and tetra-n-butylammonium bromide as the nucleophilic bromide source. The C2-brominated compounds are produced in moderate to excellent yields and with excellent regioselectivity in most cases. The potential extension of this method to other halogens, effecting C2-chlorination with Ts2O/TBACl is also presented. Finally, this method could be incorporated into a viable one-pot oxidation/bromination process, using methyltrioxorhenium/urea hydropgen peroxide as the oxidant.