35889-85-1

Upstream product

• 106-95-6 allyl bromide 
• 634-97-9 pyrrole-2-carboxyl acid 
• 107-18-6 allyl alcohol 
• 5427-82-7 1H-pyrrole-2-carbonyl chloride 

Downstream Products

• 173908-18-4 1-(5-Chloro-2-nitro-benzenesulfonyl)-1H-pyrrole-2-carboxylic acid allyl ester 
• 1000313-21-2 1-(3-chloro-4-fluoro-benzylamino)-1H-pyrrole-2-carboxylic acid allyl ester 
• 1188357-36-9 (E)-3-(benzyloxyimino)-3-cyano-2-methylpropyl 1H-pyrrole-2-carboxylate 
• 1000312-98-0 1-(4-fluoro-benzyl)-4-hydroxy-3-(7-iodo-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-3-yl)-pyrrolo[1,2-b]pyridazin-2-one 
• 1000312-97-9 1-(4-fluoro-benzylamino)-1H-pyrrole-2-carboxylic acid allyl ester 
• 1000313-22-3 1-{(3-chloro-4-fluoro-benzyl)-[2-(7-methanesulfonylmethyl-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-3-yl)-acetyl]-amino}-1H-pyrrole-2-carboxylic acid allyl ester 
• 173908-38-8 1-(2-Amino-5-chloro-benzenesulfonyl)-1H-pyrrole-2-carboxylic acid allyl ester 

Relevant academic research and scientific papers

Cobalt-Catalyzed Intermolecular Hydroamination of Unactivated Alkenes Using NFSI as Nitrogen Source

Cheap metal (Fe, Mn, and Co)-catalyzed hydroamination of alkenes has been an attractive method for synthesis of amines because of biocompatibility of metal, excellent Markovnikov selectivity and chemoselectivity. However, most reports are limited to unsaturated nitrogen sources (nitric oxide, azos, azides, cyano, etc.), for which aminated products are very limited. Notably, while used widely for fluorinating reaction, N-fluorobenzenesulfonimide (NFSI) as amine source for hydroamination has seldom been reported. Here we developed a cobalt-catalyzed intermolecular hydroamination of unactivated alkenes using NFSI as nitrogen source under mild conditions. The reaction exhibits excellent chemo- and regio-selectivity with no hydrofluorination or linear-selectivity products. Notably, the reaction proceeded with excellent yield even though the amount of Co(salen) catalyst was reduced to 0.2 mol%. Recently, a similar work was also reported by Zhang and coworkers (ref. 19).

Parameters for bromination of pyrroles in bromoperoxidase-catalyzed oxidations

Ester-, cyano-, and carboxamide-substituted 1H-pyrroles undergo electrophilic aromatic bromination, if treated with hydrogen peroxide and sodium bromide at pH 6.2 and 20 °C. Oxidation of bromide under such conditions is catalyzed by a vanadate(V)-dependent bromoperoxidase, in a substrate/enzyme ratio of 32-63 μmol %. To obtain maximum yields of bromopyrroles (up to 91%) by spending least amount of substrates and catalyst, hydrogen peroxide and sodium bromide have to be added continuously to the enzyme and the 2-acceptor-substituted pyrrole (1.5 mmol) in a solution of morpholine-4- ethanesulfonic acid buffer. This technique was applied to prepare two marine natural products under biomimetic conditions, that is, methyl 4,5-dibromopyrrole-2-carboxylate (from Agelas oroides) and 4,5-dibromopyrrole-2- carboxamide (from Acanthella carteri).

Cobalt catalyzed functionalization of unactivated alkenes: Regioselective reductive C-C bond forming reactions

(Chemical Equation Presented) The cobalt catalyzed hydroaldoximation and hydrocyanooximation of unactivated alkenes is reported. Secondary and tertiary aldoximes and oximonitriles are synthesized with excellent regioselectivity under mild conditions, and conversion of the products to valuable intermediates is documented. The reactions expand the arsenal of reductive carbon-carbon bond forming reactions as well as regioselective functionalizations of unactivated double bonds.

PYRRO[1,2-B]PYRIDAZINONE COMPOUNDS

The invention is directed to pyrro[l,2-b]pyridazinone compounds and pharmaceutical compositions containing such compounds that are useful in treating infections by hepatitis C virus.