78024-74-5

Upstream product

• 79422-01-8 tris(2-methoxyphenyl)-1,3,5,2,4,6-trioxatriborinane 
• 105-53-3 diethyl malonate 
• 6056-23-1 ethyl (2-methoxyphenyl)acetate 
• 623-49-4 ethyl cyanoformate 
• 7035-02-1 o-Methoxybenzyl chloride 
• 7035-03-2 2-methoxy-benzeneacetonitrile 
• 529-28-2 4-iodoanisol 
• 400602-58-6 2-(2-methoxy-phenyl)-3-oxo-succinic acid diethyl ester 
• 766-51-8 2-Chloroanisole 
• 578-57-4 2-bromoanisole 
• 105-58-8 Diethyl carbonate 
• 95-92-1 oxalic acid diethyl ester 
• 88612-39-9 ethyl 2-cyano-2-(2-methoxyphenyl)acetate 

Downstream Products

• 119376-10-2 4-hydroxy-7-methoxy-3-(2-methoxyphenyl)-2-quinolone 
• 20730-59-0 2-(2-methoxyphenyl)-1,3-propanediol 
• 118657-12-8 diethyl α-<1-(2-methoxyphenyl)>-α-methylmalonate 
• 81616-80-0 (S)-2(2-methoxyphenyl)propionic acid 
• 854833-35-5 (2-methoxy-phenyl)-methyl-malonic acid 
• 854647-56-6 2-(2-methoxy-phenyl)-butyric acid 
• 93-25-4 2-methoxyphenylacetic acid 
• 75256-37-0 4-hydroxy-3-(o-methoxyphenyl)-1,2-dihydroquinolin-2-one 
• 400602-59-7 4,6-dihydroxy-3-(2-methoxy-phenyl)-1H-quinolin-2-one 
• 117720-82-8 diethyl α-<1-(2-methoxyphenyl)>-α-acetoxymalonate 
• 124028-82-6 6-bromo-4-hydroxy-3-(2-methoxyphenyl)-2(1H)-quinolinone 
• 124028-80-4 6-fluoro-4-hydroxy-3-(2-methoxyphenyl)-2(1H)-quinolinone 
• 124028-81-5 6-chloro-4-hydroxy-3-(2-methoxyphenyl)-2(1H)-quinolinone 

Relevant academic research and scientific papers

Enantioselective Desymmetrization of 2-Aryl-1,3-propanediols by Direct O-Alkylation with a Rationally Designed Chiral Hemiboronic Acid Catalyst That Mitigates Substrate Conformational Poisoning

Enantioselective desymmetrization by direct monofunctionalization of prochiral diols is a powerful strategy to prepare valuable synthetic intermediates in high optical purity. Boron acids can activate diols toward nucleophilic additions; however, the design of stable chiral catalysts remains a challenge and highlights the need to identify new chemotypes for this purpose. Herein, the discovery and optimization of a bench-stable chiral 9-hydroxy-9,10-boroxarophenanthrene catalyst is described and applied in the highly enantioselective desymmetrization of 2-aryl-1,3-diols using benzylic electrophiles under operationally simple, ambient conditions. Nucleophilic activation and discrimination of the enantiotopic hydroxy groups on the diol substrate occurs via a defined chairlike six-membered anionic complex with the hemiboronic heterocycle. The optimal binaphthyl-based catalyst 1g features a large aryloxytrityl group to effectively shield one of the two prochiral hydroxy groups on the diol complex, whereas a strategically placed "methyl blocker"on the boroxarophenanthrene unit mitigates the deleterious effect of a competing conformation of the complexed diol that compromised the overall efficiency of the desymmetrization process. This methodology affords monoalkylated products in enantiomeric ratios equal or over 95:5 for a wide range of 1,3-propanediols with various 2-aryl/heteroaryl groups.

OXIDATIVE COUPLING OF ARYL BORON REAGENTS WITH SP3-CARBON NUCLEOPHILES, AND AMBIENT DECARBOXYLATIVE ARYLATION OF MALONATE HALF-ESTERS VIA OXIDATIVE CATALYSIS

Described herein are methods of oxidative coupling of aryl boron reagents with sp3-carbon nucleophiles, and ambient decarboxylative arylation of malonate half-esters via oxidative catalysis.

Oxidative Coupling of Aryl Boron Reagents with sp3-Carbon Nucleophiles: the Enolate Chan-Evans-Lam Reaction

Reported is a versatile new oxidative method for the arylation of activated methylene species. Under mild reaction conditions (RT to 40 C), Cu(OTf)2 mediates the selective coupling of functionalized aryl boron species with a variety of stabilized sp3-nucl

Oxidative coupling of aryl boron reagents with sp3-carbon nucleophiles: The enolate chan–evans–lam reaction

Reported is a versatile new oxidative method for the arylation of activated methylene species. Under mild reaction conditions (RT to 40°C), Cu(OTf)2mediates the selective coupling of functionalized aryl boron species with a variety of stabilized sp3-nucleophiles. Tertiary malonates and amido esters can be employed as substrates to generate quaternary centers. Complementing either traditional cross-coupling or SNAr protocols, the transformation is chemoselective in the presence of halogen electrophiles, including aryl bromides and iodides. Substrates bearing amide, sulfonyl, and phosphonyl groups, which are not amenable to coupling under mild Hurtley-type conditions, are suitable reaction partners.

New efficient ligand-free, copper nanoparticle catalyzed coupling reactions of aryl halides with diethyl malonate to produce α-arylation of malonates

Recently synthesized copper nanoparticles (Cu NP) were used to catalyze coupling of aryl halides with diethyl malonates to produce α-aryl malonates. Synthetic conditions, including solvents, relative amounts of reactants, catalyst, and temperature, etc. h

Arylation with unsymmetrical diaryliodonium salts: A chemoselectivity study

Phenols, anilines, and malonates have been arylated under metal-free conditions with twelve aryl(phenyl)iodonium salts in a systematic chemoselectivity study. A new "anti-ortho effect" has been identified in the arylation of malonates. Several "dummy groups" have been found that give complete chemoselectivity in the transfer of the phenyl moiety, irrespective of the nucleophile. An aryl exchange in the diaryliodonium salts has been observed under certain arylation conditions. DFT calculations have been performed to investigate the reaction mechanism and to elucidate the origins of the observed selectivities. These results are expected to facilitate the design of chiral diaryliodonium salts and the development of catalytic arylation reactions that are based on these sustainable and metal-free reagents. Copyright

Enzymatic desymmetrization of prochiral 2-substituted-1,3-diamines: Preparation of valuable nitrogenated compounds

A wide range of prochiral 1, 3-diamines were first efficiently synthesized and subsequently desymmetrized by using lipase from Pseudomonas cepacia as catalyst and diallyl carbonate as alkoxycarbonylating agent. In all cases, the amino carbamates of R-configuration were recovered. Final selective cleavage of the N-allyloxycarbonyl moiety was carried out under mild reaction conditions, which demonstrates the high versatility and potential of this chemoenzymatic route as a source of intermediates in the synthesis of related optically active nitrogenated derivatives.

Copper(I)-catalyzed C-C and C-O coupling reactions using hydrazone ligands

Copper-catalyzed C-C coupling reaction of aryl iodides with diethylmalonate in toluene at 90C gave arylated malonates using 5 mol% of CuI with hydrazone 1a as a ligand in good yields under an aerobic atmosphere. We also found CuI/hydrazone 1b in toluene to be an efficient catalytic system for C-O coupling reactions of aryl bromides with phenols to give aryl ethers in good yields at 110C under an aerobic atmosphere.

Room-temperature copper-catalyzed α-arylation of malonates

An effective method in targeting α-aryl malonates is reported. In the presence of a catalytic amount of 2-picolinic acid and Cul, the coupling of aryl iodides with diethyl malonate proceeds smoothly even at room temperature. The high levels of functional group compatibility and exceptionally mild reaction conditions offer this an attractive protocol in accessing a variety of arylated malonates.

KERATINOCYTE GROWTH FACTOR RECEPTOR - TYROSINE SPECIFIC INHIBITORS FOR THE PREVENTION OF CANCER METASTATIS

Compounds and methods for treating, inhibiting, or delaying the onset of cancer in subject by administering a therapeutically effective amount of a keratinocyte growth facto receptor tyrosine kinase (KGFR TK) inhibitor to the subject in need of such treatment. Als provided are compounds and methods for the treating, inhibiting, or delaying the onset o metastasis in a subject with cancer by administering a therapeutically effective amount of KGFR TK inhibitor to the subject in need of such treatment.