17078-29-4

Upstream product

• 586-77-6 4-bromo-N,N-dimethylaniline 
• 6148-64-7 ethyl potassium malonate 
• 698-69-1 4-chloro-N,N-dimethylaniline 
• 5764-82-9 bromo(2-ethoxy-2-oxoethyl)zinc 
• 105-53-3 diethyl malonate 
• 64-17-5 ethanol 
• 17078-28-3 2-[4-(dimethylamino)phenyl]acetic acid 

Downstream Products

• 1027978-94-4 3-(6-chloro-pyridin-3-yl)-2-(4-dimethylamino-phenyl)-3-oxo-propionic acid ethyl ester 
• 83026-39-5 diethyl <4-(dimethylamino)phenyl>propanedioate 
• 1027087-85-9 6-amino-4-(3-chloro-phenyl)-3-(4-dimethylamino-phenyl)-6'-morpholin-4-yl-[2,3']bipyridinyl-5-carbonitrile 
• 1026950-17-3 2-(4-dimethylamino-phenyl)-1-(6-morpholin-4-yl-pyridin-3-yl)-ethanone 
• 1026404-43-2 1-(6-chloro-pyridin-3-yl)-2-(4-dimethylamino-phenyl)-ethanone 
• 926008-73-3 {4-[5-(4-dimethylaminophenyl)-6-chloropyrimidin-4-ylethynyl]phenyl}dimethylamine 
• 926008-60-8 [4-(4,6-dichloropyrimidin-5-yl)phenyl]dimethylamine 
• 926008-53-9 5-(4-dimethylaminophenyl)pyrimidine-4,6-diol 

Relevant academic research and scientific papers

Copper-Catalyzed Ullmann-Type Coupling and Decarboxylation Cascade of Arylhalides with Malonates to Access α-Aryl Esters

We have developed a high-efficiency and practical Cu-catalyzed cross-coupling to directly construct versatile α-aryl-esters by utilizing readily available aryl bromides (or chlorides) and malonates. These gram-scale approaches occur with turnovers of up to 1560 and are smoothly conducted by the usage of a low catalyst loading, a new available ligand, and a green solvent. A variety of functional groups are tolerated, and the application occurs with α-aryl-esters to access nonsteroidal anti-inflammatory drugs (NSAIDs) on the gram scale.

Coupling of Reformatsky Reagents with Aryl Chlorides Enabled by Ylide-Functionalized Phosphine Ligands

The coupling of aryl chlorides with Reformatsky reagents is a desirable strategy for the construction of α-aryl esters but has so far been substantially limited in the substrate scope due to many challenges posed by various possible side reactions. This limitation has now been overcome by the tailoring of ylide-functionalized phosphines to fit the requirements of Negishi couplings. Record-setting activities were achieved in palladium-catalyzed arylations of organozinc reagents with aryl electrophiles using a cyclohexyl-YPhos ligand bearing an ortho-tolyl-substituent in the backbone. This highly electron-rich, bulky ligand enables the use of aryl chlorides in room temperature couplings of Reformatsky reagents. The reaction scope covers diversely functionalized arylacetic and arylpropionic acid derivatives. Aryl bromides and chlorides can be converted selectively over triflate electrophiles, which permits consecutive coupling strategies.

Pd-catalyzed decarboxylative cross-couplings of potassium malonate monoesters with aryl halides

An efficient catalytic protocol for Pd-catalyzed decarboxylative cross-coupling of potassium malonate monoesters and derivatives with aryl bromides and chlorides are described. Because of its broad applicability, this new catalytic system provides an alternative method for the preparation of diverse aryl acetic acids and derivatives.

COMPOUNDS FOR THE REDUCTION OF β-AMYLOID PRODUCTION

The present disclosure provides a series of compounds of the formula (I), which modulate β-amyloid peptide (β-ΑΡ) production and are useful in the treatment of Alzheimer's Disease and other conditions affected by β-amyloid peptide (β-ΑΡ) production.

Practical synthesis of 2-arylacetic acid esters via palladium-catalyzed dealkoxycarbonylative coupling of malonates with aryl halides

A new palladium-based system was developed that catalyzes the coupling of aryl halides with diethyl malonates in the presence of mild bases. In the course of the reaction, the intermediately formed diethyl arylmalonate is directly converted into the arylacetic acid ester via liberation of carbon dioxide and an alkanol. This cross-coupling/dealkoxycarbonylation process provides an efficient and high-yielding synthetic entry to diversely functionalized arylacetic acid esters. Two complementary protocols were developed, one of which is optimal for electron-rich, the other for electron-poor aryl halides. Both make use of low loadings of palladium(0) bis(dibenzylideneacetone) (0.5 mol%)/tri-tert-butylphosphonium tetrafluoroborate (1.1 mol%) as the catalyst and diethyl malonate as the reaction solvent. The new procedures are particularly effective for sterically hindered substrates. Copyright

4-Amino-5-aryl-6-arylethynylpyrimidines: Structure-activity relationships of non-nucleoside adenosine kinase inhibitors

A series of non-nucleoside adenosine kinase (AK) inhibitors is reported. These inhibitors originated from the modification of 5-(3-bromophenyl)-7-(6-morpholin-4-ylpyridin-3-yl)pyrido[2,3-d]pyrimidin-4-ylamine (ABT-702). The identification of a linker that would approximate the spatial arrangement found between the pyrimidine ring and the aryl group at C(7) in ABT-702 was a key element in this modification. A search of potential linkers led to the discovery of an acetylene moiety as a suitable scaffold. It was hypothesized that the aryl acetylenes, ABT-702, and adenosine bound to the active site of AK (closed form) in a similar manner with respect to the orientation of the heterocyclic base. Although potent acetylene analogs were discovered based on this assumption, an X-ray crystal structure of 5-(4-dimethylaminophenyl)-6-(6-morpholin-4-ylpyridin-3-ylethynyl)pyrimidin-4-ylamine (16a) revealed a binding orientation contrary to adenosine. In addition, this compound bound tightly to a unique open conformation of AK. The structure-activity relationships and unique ligand orientation and protein conformation are discussed.