5021-60-3

Usage

Uses

Used in Pharmaceutical and Medicinal Chemistry:
N-(4-fluorophenyl)-4-methoxybenzamide is utilized as a building block in the synthesis of various organic compounds, contributing to the development of new pharmaceutical agents. Its unique structure allows for the creation of diverse molecules with potential therapeutic properties.
Used in Enzyme Inhibition:
N-(4-fluorophenyl)-4-methoxybenzamide may serve as an enzyme inhibitor, potentially modulating biological pathways and offering therapeutic benefits in treating specific diseases. Its precise mechanism of action and target enzymes would require further research to elucidate its full potential in this application.
Used in Biological Pathway Modulation:
As a modulator of biological pathways, N-(4-fluorophenyl)-4-methoxybenzamide could be employed to regulate cellular processes and responses, which may have implications in the treatment of various conditions. The specific pathways and effects would need to be determined through additional studies.
Further research and studies are necessary to fully understand the range of applications and potential benefits of N-(4-fluorophenyl)-4-methoxybenzamide in different fields, ensuring its safe and effective use in pharmaceutical and medicinal applications.

InChI:InChI=1/C14H12FNO2/c1-18-13-8-2-10(3-9-13)14(17)16-12-6-4-11(15)5-7-12/h2-9H,1H3,(H,16,17)

Upstream product

• 100-07-2 4-methoxy-benzoyl chloride 
• 371-40-4 4-fluoroaniline 
• 696-63-9 4-Methoxybenzenethiol 
• 201230-82-2 carbon monoxide 
• 696-62-8 para-iodoanisole 
• 1195-45-5 para-fluorophenyl isocyanate 
• 254454-47-2 4-methoxyphenylzinc iodide 
• 345-89-1 4-fluoro-4'-methoxybenzophenone 
• 38695-26-0 1-(4-fluorobenzyl)-4-methoxybenzene 
• 352-34-1 4-fluoro-1-iodobenzene 
• 2393-23-9 4-methoxy-benzylamine 

Downstream Products

• 1017572-83-6 (Z)-4-fluoro-N-(1-(4-methoxyphenyl)-3-(trimethylsilyl)prop-2-ynylidene)aniline 

Relevant academic research and scientific papers

Cobalt catalysed aminocarbonylation of thiols in batch and flow for the preparation of amides

The synthesis of amides from thiols through a cobalt-catalyzed aminocarbonylation is shown. After optimizing all the reaction parameters, the methodology makes possible the obtention of amides with variable yields, while competing reactions such as the formation of disulfides and ureas can be limited. The process works well with aromatic thiols with electron donating groups (EDG) whereas other thiols give reaction with lower yields. The previous process has been transferred and optimized into flow equipment, thus allowing using less CO in a safer way, and permitting the scaling up of the synthesis. Two drugs, moclobemide and itopride were prepared with this methodology, albeit only in the second case with good results. A mechanistic pathway is proposed.

Rhodium-Catalyzed Addition of Organozinc Iodides to Carbon-11 Isocyanates

Amides were prepared using rhodium-catalyzed coupling of organozinc iodides and carbon-11 (11C, t1/2 = 20.4 min) isocyanates. Nonradioactive isocyanates and sp3 or sp2 organozinc iodides generated amides in yields of 13%-87%. Incorporation of cyclotron-produced [11C]CO2 into 11C-amide products proceeded in yields of 5%-99%. The synthetic utility of the methodology was demonstrated through the isolation of [11C]N-(4-fluorophenyl)-4-methoxybenzamide ([11C]6g) with a molar activity of 267 GBq μmol-1 and 12% radiochemical yield in 21 min from the beginning of synthesis.

Microdroplets as Microreactors for Fast Synthesis of Ketoximes and Amides

The formation of amide bonds is one of the most valuable transformations in organic synthesis. Beckmann rearrangement is a well-known method for producing secondary amides from ketoximes. This study demonstrates the rapid synthesis of ketoximes and amides in microdroplets. Many factors are found to affect the yield, such as microdroplet generation devices, temperature, catalysts, and concentrations of reactants. In particular, the temperature has a great influence on the synthesis of amide, which is demonstrated by a sharp ascendance to the yield when the temperature was increased to 45 °C. The best amide yield (93.3%) can be obtained by using coaxial flowing devices, a sulfonyl chloride compound as a catalyst, and heating to 55 °C in microdroplets. The yields can reach 78.7-91.3% for benzoylaniline and 87.2-93.4% for benzophenone oximes in several seconds in microdroplets compared to 10.1-66.1% and 82.5-93.3% in several hours in the bulk phase. Apart from the dramatically decreased reaction time and enhanced reaction yields, the microdroplet synthesis is also free of severe reaction environments (anhydrous and anaerobic conditions). In addition, the synthesis in microdroplets also saves reactants and solvents and reduces the waste amounts. All of these merits indicate that the microdroplet synthesis is a high-efficiency green methodology.

Hypervalent Iodine-Mediated Oxidative Rearrangement of N-H Ketimines: An Umpolung Approach to Amides

An umpolung approach to amides via hypervalent iodine-mediated oxidative rearrangement of N-H ketimines under mild reaction conditions is described. This strategy provides target amides with excellent selectivity in good yields. In addition, preliminary m

Amide compound with antitumor activity and application of amide compound

The invention belongs to the technical field of pharmaceutical chemistry and particularly provides an amide compound with antitumor activity and application of the amide compound. The structural formula of the amide compound is shown as R1CONHR2, wherein R1 and R2 are independently selected from aryl or heterocycle. The biological activity test result of the compound shows that the compound has a good inhibition effect on histone methyl SET7. Good antitumor aspect development application prospects are achieved.

Lewis acid-assisted N-fluorobenzenesulfonimide-based electrophilic fluorine catalysis in Beckmann rearrangement

A microwave-assisted N-fluorobenzenesulfonimide (NFSI)/Lewis acid-catalyzed Beckmann rearrangement was developed. The remarkable promotion to the electrophilicity of NFSI by Lewis acids was illustrated utilizing a series of readily available oxime substrates. The action model between NFSI and Lewis acids was probed by control experiments and theoretical calculations.

Oxidative fluorination of N-arylsulfonamides

We report a late stage oxidative nucleophilic fluorination of N-arylsulfonamides, a class of compounds so far not considered as precursors to 4-fluorophenyl sulfonamides. By installing a para-positioned tert-butyl substituent on the aniline, oxidative fluorination takes place regioselectively in the presence of HF·pyridine and PIDA. This methodology has been shown to give good yields for a variety of ortho- and meta-functionalised N-arylsulfonamides and has been adapted for radiofluorination to give 4-[18F]fluorophenyl sulfonamides under carrier added conditions.

DDQ-promoted direct transformation of benzyl hydrocarbons to amides via tandem reaction of the CDC reaction and Beckmann rearrangement

An atom-efficient and transition metal-free approach to amides from the corresponding benzyl hydrocarbons through C-H and C-C bond cleavage has been developed. Mechanistic studies have shown that a DDQ-promoted cross-dehydrogenative coupling (CDC) reaction with subsequent oxidation and rearrangement are involved in this transformation. The Royal Society of Chemistry.

The synthesis of N-arylated amides via copper(II) triflate-catalyzed direct oxygenation and N-arylation of benzylamines with aryl iodides

An efficient approach for the synthesis of N-arylated amides by copper(II) triflate-catalyzed direct oxygenation and N-arylation reaction of benzylamines with aryl iodides is reported. Various benzylamines and aryl iodides can participate in the reaction, providing a series of N-arylated amides in moderate to good yields.

The synthesis of N-arylated amides via copper(II) triflate-catalyzed direct oxygenation and N-arylation of benzylamines with aryl iodides

An efficient approach for the synthesis of N-arylated amides by copper(II) triflate-catalyzed direct oxygenation and N-arylation reaction of benzylamines with aryl iodides is reported. Various benzylamines and aryl iodides can participate in the reaction, providing a series of N-arylated amides in moderate to good yields.