189161-09-9Relevant academic research and scientific papers
Palladium-Catalyzed Cyanation under Mild Conditions: A Case Study to Discover Appropriate Substrates among Halides and Pseudohalides
Rajendra, Merla Arjuna,Sunil,Sajith, Ayyiliath Meleveetil,Joy, Muthipeedika Nibin,Bakulev, Vasiliy A.,Haridas, Karickal Raman
supporting information, p. 1629 - 1633 (2020/09/15)
A case study has been effectively carried out to identify a suitable substrate among halides and pseudohalides for the palladium-catalyzed cyanation reactions under mild conditions. Among the various substrates considered for evaluation, aryl pentafluorobenzenesulfonates and nonaflates were identified to be the best substrates when compared to corresponding halides and pseudohalides. The substoichiometric use of nontoxic, environmentally benign potassium hexacyanoferrate as a cyanide source and exceptionally milder conditions further highlights the significance of the protocol developed. A wide range of electronically biased and sterically challenging substrates provided the corresponding the nitriles in good to excellent yields.
COMPOUNDS AND USES THEREOF
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Page/Page column 164-165, (2020/10/20)
The present invention features compounds useful in the treatment of neurological disorders and primary brain cancer. The compounds of the invention, alone or in combination with other pharmaceutically active agents, can be used for treating or preventing neurological disorders and primary brain cancer.
COMPOUNDS AND USES THEREOF
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Page/Page column 158, (2019/10/15)
The present invention features compounds useful in the treatment of neurological disorders. The compounds of the invention, alone or in combination with other pharmaceutically active agents, can be used for treating or preventing neurological disorders.
Cyanation of arenes via iridium-catalyzed borylation
Liskey, Carl W.,Liao, Xuebin,Hartwig, John F.
supporting information; experimental part, p. 11389 - 11391 (2010/10/01)
We report a method to conduct one-pot meta cyanation of arenes by iridium-catalyzed C-H borylation and copper-mediated cyanation of the resulting arylboronate esters. This process relies on a method to conduct the cyanation of arylboronic esters, and conditions for this new transformation are reported. Conditions for the copper-mediated cyanation of arylboronic acids are also reported. By the resulting sequence of borylation and cyanation, 1,3-disubstituted and 1,2,3-trisubstituted arenes and heteroarenes containing halide, ketone, ester, amide, and protected alcohol functionalities are converted to the corresponding meta-substituted aryl nitriles. The utility of this methodology is demonstrated through the conversion of a protected 2,6-disubstituted phenol to 4-cyano-2,6-dimethylphenol, which is an intermediate in the synthesis of the pharmaceutical etravirine. The utility of the method is further demonstrated by the conversion of 3-chloro-5-methylbenzonitrile, produced through the one-pot C-H borylation and cyanation sequence, to the corresponding 3,5-disubstituted aldehydes, ketones, amides, carboxylic acids, tetrazoles, and benzylamines.
PYRIDONE DERIVATIVES AS NON-NUCLEOSIDE REVERSE TRANSCRIPTASE INHIBITORS
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Page/Page column 40, (2010/04/03)
The present invention relates to 2-pyridone derivatives of Formula (I) or (IV) as herein described, compositions containing such compounds, synthetic processes for making such compounds, and therapeutic methods that include the administration of such comp
Meta halogenation of 1,3-disubstituted arenes via iridium-catalyzed arene borylation
Murphy, Jaclyn M.,Liao, Xuebin,Hartwig, John F.
, p. 15434 - 15435 (2008/09/19)
We report the meta halogenation of 1,3-disubstituted arenes to form 3,5-disubstituted aryl bromides and chlorides by using iridium-catalyzed arene borylation chemistry. Iridium-catalyzed borylation of arenes with B2pin2, followed by reaction of the boronic ester with copper(II) bromide or chloride converts arylboronic esters to the corresponding aryl halides. A variety of arenes containing alkoxy, alkyl, halogen, nitrile, ester, amide, and pivaloyl and TIPS-protected alcohols were converted to the corresponding 3,5-disubstituted aryl bromides and chlorides in yields ranging from 46% to 85%. In addition, 2,6-disubstituted and 3-substituted pyridines were converted to the 4-halo and 5-halopyridines, respectively. The utility of this methodology was demonstrated by the formal conversion of nicotine to Altinicline in three steps with an overall yield of 61% using meta bromination of nicotine as the first step. Copyright
1,2-Diarylimidazoles as potent, cyclooxygenase-2 selective, and orally active antiinflammatory agents
Khanna, Ish K.,Weier, Richard M.,Yu, Yi,Xu, Xiang D.,Koszyk, Francis J.,Collins, Paul W.,Koboldt, Carol M.,Veenhuizen, Amy W.,Perkins, William E.,Casier, Jacquelen J.,Masferrer, Jaime L.,Zhang, Yan Y.,Gregory, Susan A.,Seibert, Karen,Isakson, Peter C.
, p. 1634 - 1647 (2007/10/03)
Series of 1,2-diarylimidazoles has been synthesized and found to contain highly potent and selective inhibitors of the human COX-2 enzyme. The paper describes a short synthesis of the target 1,2-diarylimidazoles starting with aryl nitriles. Different portions of the diarylimidazole (I) were modified to establish SAR. Systematic variations of the substituents in the aryl ring B have yielded very potent (IC50 = 10-100 nm) and selective (1000-12500) inhibitors of the COX-2 enzyme. The study on the influence of substituents in the imidazole ring established that a CF3 group at position 4 gives the optimum oral activity. A number of the diarylimidazoles showed excellent inhibition in the adjuvant induced arthritis model (e.g., ED50 = 0.02 mpk for 22 and 34). The diarylimidazoles are also potent inhibitors of carrageenan-induced edema (ED50 = 9-30 mpk) and hyperalgesia (ED50 = 11- 40 mpk). Several orally active diarylimidazoles show no GI toxicity in the rat and mouse up to 200 mpk.
