56969-31-4

Upstream product

• 1736-67-0 4-fluorophenylacetaldehyde 
• 95-54-5 1,2-diamino-benzene 
• 725-49-5 2-(4-fluoro-benzyl)-1H-benzoimidazole 
• 51-17-2 benzoimidazole 
• 1194-02-1 4-fluorobenzonitrile 
• 122-51-0 orthoformic acid triethyl ester 
• 35538-21-7 2-(4-fluoro-α-hydroxybenzyl)benzimidazole 

Downstream Products

• 56969-25-6 C₁₇H₁₃FN₂O₂ 

Relevant academic research and scientific papers

Selective Oxidation of Alkylarenes to the Aromatic Ketones or Benzaldehydes with Water

Here a palladium-catalyzed oxidation method for converting alkylarenes into the aromatic ketones or benzaldehydes with water as the only oxygen donor is reported. This C-H bond oxidation functionalization does not require other oxidants and hydrogen accep

Selective Electrochemical Oxygenation of Alkylarenes to Carbonyls

An efficient electrochemical method for benzylic C(sp3)-H bond oxidation has been developed. A variety of methylarenes, methylheteroarenes, and benzylic (hetero)methylenes could be converted into the desired aryl aldehydes and aryl ketones in moderate to excellent yields in an undivided cell, using O2 as the oxygen source and lutidinium perchlorate as an electrolyte. On the basis of cyclic voltammetry studies, 18O labeling experiments, and radical trapping experiments, a possible single-electron transfer mechanism has been proposed for the electrooxidation reaction.

Selective synthesis of (1: H-benzo [d] imidazol-2-yl)(phenyl)methanone and quinoxaline from aromatic aldehyde and o-phenylenediamine

We have designed a general, inexpensive, and versatile method for the synthesis of (1H-benzo[d]imidazol-2-yl)(phenyl)methanone and the formation of C-N bonds via an aromatic aldehyde and o-phenylenediamine. In the presence of N,N-dimethylformamide/sulfur, (1H-benzo[d]imidazol-2-yl)(phenyl)methanone was obtained; however, in the absence of sulfur, quinoxaline was obtained in 1,4-dioxane. A wide range of quinoxalines and (1H-benzo[d]imidazol-2-yl)(phenyl)methanones was obtained under mild conditions.

Co/NHPI-mediated aerobic oxygenation of benzylic C-H bonds in pharmaceutically relevant molecules

A simple cobalt(ii)/N-hydroxyphthalimide catalyst system has been identified for selective conversion of benzylic methylene groups in pharmaceutically relevant (hetero)arenes to the corresponding (hetero)aryl ketones. The radical reaction pathway tolerates electronically diverse benzylic C-H bonds, contrasting recent oxygenation reactions that are initiated by deprotonation of a benzylic C-H bond. The reactions proceed under practical reaction conditions (1 M substrate in BuOAc or EtOAc solvent, 12 h, 90-100 °C), and they tolerate common heterocycles, such as pyridines and imidazoles. A cobalt-free, electrochemical, NHPI-catalyzed oxygenation method overcomes challenges encountered with chelating substrates that inhibit the chemical reaction. The utility of the aerobic oxidation method is showcased in the multigram synthesis of a key intermediate towards a drug candidate (AMG 579) under process-relevant reaction conditions.

The design, synthesis, and biological evaluation of potent receptor tyrosine kinase inhibitors

Variously substituted indolin-2-ones were synthesized and evaluated for activity against KDR, Flt-1, FGFR-1 and PDGFR. Extension at the 5-position of the oxindole ring with ethyl piperidine (compound 7i) proved to be the most beneficial for attaining both biochemical and cellular potencies. Further optimization of 7i to balance biochemical and cellular potencies with favorable ADME/ PK properties led to the identification of 8h, a compound with a clean CYP profile, acceptable pharmacokinetic and toxicity profiles, and robust efficacy in multiple xenograft tumor models.

Synthesis and pharmacological properties of analogs of oxapadol, a new analgesic agent

A series of various heterocyclic compounds related to Oxapadol was prepared and evaluated for analgesic activity in mice. Some of them possessed significant analgesic effects; their structure activity relationships and chemistry are discussed. These compounds represent, in the authors' opinion, a unique series of analgesic agents.