77120-14-0

Upstream product

• 107-13-1 acrylonitrile 
• 540-37-4 p-aminoiodobenzene 
• 106-40-1 4-bromo-aniline 
• 198995-94-7 N-[4-((E)-2-Cyano-vinyl)-phenyl]-acetamide 

Downstream Products

• 17570-30-8 trans-p-aminocinnamic acid 
• 10139-91-0 3-(4-aminophenyl)-propionitrile 

Relevant academic research and scientific papers

In situ generation of palladium nanoparticles: Reusable, ligand-free heck reaction in PEG-400 assisted by focused microwave irradiation

A rapid and efficient Heck coupling reaction of aryl iodides with terminal olefins was conducted in PEG-400 at 120 °C in the presence of potassium carbonate and palladium nanoparticles formed in situ from palladium chloride under focused microwave irradiation. High to excellent product yields were achieved. The reaction medium and catalyst could be easily recycled at least five times without significant loss in reactivity. Georg Thieme Verlag Stuttgart New York.

Ligandless Heck coupling between a halogenated aniline and acrylonitrile catalyzed by Pd/C: Development and optimization of an industrial-scale Heck process for the production of a pharmaceutical intermediate

The aniline derivative 3 is a key building block of rilpivirine (TMC278) 2, a new potent NNRTI compound under clinical evaluation. In this paper we describe the development of a new synthesis of 3 based on a Heck coupling between a halogenated aniline and acrylonitrile using low loading of Pd/C (0.5 mol %) as catalyst. This resulted in a process which has been successfully transferred into production on 2400 mol-scale (6000 L reactor)

HIV INHIBITING 1,2,4-TRIAZIN-6-ONE DERIVATIVES

The present invention relates to HIV replication inhibitors of formula (I) a N-oxide, a pharmaceutically acceptable addition salt, a quaternary amine or a stereochemically isomeric form thereof, wherein ring A and ring B represent phenyl, pyridyl, pyridaz

MODIFIED HECK REACTION

The present invention includes a method for the preparation of a cinnamonitrile by addition of an aryl to acrylonitrile in the presence of a heterogeneous palladium catalyst, a phosphine, a base and a salt. The reaction can be conducted not only on aryl compounds activated with electron withdrawing groups, but also on neutral and even on deactivated aryl compounds.

Stereospecific Preparation of (E) and (Z)-3,3-Diarylacrylonitriles by Heck Reaction

Both isomers 5 and 8 of 3,3-diarylacrylonitrile constitution are obtained in highly diastereoselective Pd-catalyzed Heck reactions under Jeffery conditions between (E)-cinnamonitriles and aryl iodides.

Benzene-azo-heterocyclic dyestuffs derived from alkyl aminocinnamates or aminocinnamide

A dyestuff of the formula: STR1 IN WHICH --CH=CH--CO--Y is fixed in the 4 or 5 position, X is hydrogen or chlorine, Y is amino or alkoxy containing 1 to 4 carbon atoms, the p-phenylene nucleus A is unsubstituted or substituted by chlorine, alkyl containing 1 to 4 carbon atoms, alkoxy containing 1 to 4 carbon atoms, formylamino, acetylamino, propanoylamino, benzoylamino or cinnamoylamino, m is 0 or 1, and B represents the radical N-methyl (or ethyl)-4-hydroxy-2-oxo-quinolyl, 2-hydroxy-carbazolyl, 3-hydroxy-dibenzofuranyl, 2-phenylindolyl, N-methyl (or ethyl)-2-hydroxy-3-cyano-4-methyl-6-oxopyridyl, 3,6-dimethyl-4-hydroxy-1-phenyl-(4,5,-b)pyrazolopyridyl or the radical of formula: STR2 wherein R3 is hydrogen, methyl, alkoxycarbonyl, carbonamido or alkyl-substituted carbonamido and R4 is hydrogen, chlorine, nitro, methyl, cyano or, but only in the 3 or 4 position of the phenyl nucleus, sulphonamido, carbonamido, alkyl-substituted sulphonamido or alkyl-substituted carbonamido, the alkyl and alkoxy groups containing 1 to 4 carbon atoms. Such a dyestuff is used in the coloration of synthetic fibres.