57993-17-6

Upstream product

• 20357-28-2 5-chloro-2-nitro-trans-cinnamic acid 
• 6628-86-0 5-chloro-2-nitrobenzaldehyde 
• 1635-61-6 5-chloro-2-nitroaniline 
• 292638-85-8 acrylic acid methyl ester 

Downstream Products

• 231296-03-0 methyl (2E)-3-(2′-amino-5′-chlorophenyl)prop-2-enoate 
• 618902-24-2 [5-chloro-2-(4-chloro-benzoyl)-1H-indol-3-yl]-acetic acid methyl ester 
• 231296-04-1 methyl trans-5-chloro-2-(phenylsulfonylamino)cinnamate 

Relevant academic research and scientific papers

Multibond Forming Tandem Reactions of Anilines via Stable Aryl Diazonium Salts: One-Pot Synthesis of 3,4-Dihydroquinolin-2-ones

A fast and effective one-pot tandem process that generates Heck coupled products from readily available anilines via stable aryl diazonium tosylate salts was developed. The mild and simple procedure involves rapid formation of aryl diazonium salts using a polymer-supported nitrite reagent and p-tosic acid, followed by a base-free Heck-Matsuda coupling with acrylates and styrenes. Using 2-nitroanilines as substrates, the one-pot tandem process was extended for the direct synthesis of 3,4-dihydroquinolin-2-ones. In this case, following diazotization and Heck-Matsuda coupling to give methyl cinnamates, addition of hydrogen and reutilization of the palladium catalyst for reduction of the nitro group and hydrogenation of the alkene resulted in efficient formation of 3,4-dihydroquinolin-2-ones. The synthetic utility of this one-pot, four-stage process was demonstrated with the five-pot synthesis of a quinolinone-based sodium ion channel modulator.

2,3-substituted indole compounds as anti-inflammatory and analgesic agents

This invention provides a compound of the following formula: or the pharmaceutically acceptable salts thereof wherein Z is OH, C1-6 alkoxy, —NR2R3 or heterocycle; Q is selected from the following: (a) an optionally substituted phenyl, (b) an optionally substituted 6-membered monocyclic aromatic group containing one, two, three or four nitrogen atom(s), (c) an optionally substituted 5-membered monocyclic aromatic group containing one heteroatom selected from O, S and N and optionally containing one, two or three nitrogen atom(s) in addition to said heteroatom, (d) an optionally substituted C3-7 cycloalkyl and (e) an optionally substituted benzo-fuzed heterocycle; R1 is hydrogen, C1-4 alkyl or halo; R2 and R3 are independently hydrogen, OH, C1-4 alkoxy, C1-4 alkyl or C1-4 alkyl substituted with halo, OH, C1-4 alkoxy or CN; X is independently selected from H, halo, C1-4 alkyl, halo-substituted C1-4 alkyl, OH, C1-4 alkoxy, halo-substituted C1-4 alkoxy, C1-4 alkylthio, NO2, NH2, di-(C1-4 alkyl)amino and CN; and n is 0, 1, 2, 3 and 4.This invention also provides a pharmaceutical composition useful for the treatment of a medical condition in which prostaglandins are implicated as pathogens.

Tetrazolylalkyl indole compounds as anti-inflammatory and analgesic agents

This invention provides a compound of the following formula: or the pharmaceutically acceptable salts thereof wherein Z is tetrazolyl optionally substituted with a substituent selected from C1-4 alkyl and halosubstituted C1-4 alkyl;A is C1-6 alkylene; Q is selected from the following groups: (a) optionally substituted phenyl; (b) an optionally substituted, partially saturated, fully saturated or fully unsaturated five to six membered monocyclic group having one to three heteroatoms; and (c) an optionally substituted, bicyclic group consisting of two fused partially saturated, fully saturated or fully unsaturated five or six membered rings independently and optionally having one to four heteroatoms; X is halogen, C1-4 alkyl, halosubstituted C1-4 alkyl, OH, C1-4 alkoxy or the like; and n is 0, 1, 2, 3 or 4. This invention also provides a pharmaceutical composition useful for the treatment of a medical condition in which prostaglandins are implicated as pathogens.