96719-99-2

Usage

InChI:InChI=1/C14H11FO2/c1-17-13-7-5-10(6-8-13)14(16)11-3-2-4-12(15)9-11/h2-9H,1H3

Upstream product

• 100-66-3 methoxybenzene 
• 1711-07-5 3-fluorobenzoyl chloride 
• 38158-78-0 (3-fluorophenyl)(4-methoxyphenyl)methanol 
• 201230-82-2 carbon monoxide 
• 696-62-8 para-iodoanisole 
• 67-66-3 chloroform 
• 768-35-4 3-fluorophenylboronic acid 
• 17318-03-5 bromo(3-fluorophenyl)magnesium 
• 123-11-5 4-methoxy-benzaldehyde 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 1121-86-4 1-Fluoro-3-iodobenzene 
• 50978-45-5 3-oxobenzo[d]isothiazole-2(3H)-carbaldehyde 1,1-dioxide 
• 5720-07-0 4-methoxyphenylboronic acid 
• 1073-06-9 3-fluorobromobenzene 

Downstream Products

• 38158-78-0 (3-fluorophenyl)(4-methoxyphenyl)methanol 
• 1446099-60-0 (4-(3-chloropropoxy)phenyl)(3-fluorophenyl)methanone 
• 1446099-50-8 (R)-(3-fluorophenyl)(4-(3-(2-methylpyrrolidin-1-yl)propoxy)phenyl)methanone 
• 96835-13-1 C₁₄H₁₂ClFO 
• 460747-40-4 (3-fluorophenyl)(4-hydroxy-3-iodophenyl)methanone 
• 190728-34-8 (3-fluorophenyl)(4-hydroxyphenyl)methanone 
• 96719-85-6 [1-(3-Fluoro-phenyl)-1-(4-methoxy-phenyl)-meth-(Z)-ylidene]-phenyl-amine 

Relevant academic research and scientific papers

Palladium Catalyzed Carbonylative Coupling for Synthesis of Arylketones and Arylesters Using Chloroform as the Carbon Monoxide Source

We describe a modular, palladium catalyzed synthesis of aryl(hetero)aryl benzophenones and aryl benzoates from aryl(hetero)aryl halides using CHCl3 as the carbonyl source in the presence of KOH. The reaction occurs in tandem through an initial carbonylation to generate an aroyl halide, which undergoes coupling with arylboronic acids, bornonates, and phenols. Direct carbonylative coupling of indoles at the third position has also been accomplished under slightly modified reaction conditions by in situ activation of the C-H bond. Notably, CHCl3 is a convenient and safe alternation of CO gas, provides milder reaction conditions with high functional group tolerance, and gives the products in moderate to good yields.

Base free Suzuki acylation reactions of sodium (aryl trihydroxyborate) salts: A novel synthesis of substituted aryl ketones

The first simple and efficient base free Pd(PPh3)4 catalysed synthesis of substituted aryl ketones from acyl chlorides and easily accessible sodium aryl trihydroxyborate salts in aqueous toluene is reported. The reaction conditions appeared versatile and tolerable to a variety of functional groups including, CF3, OMe, SMe, Br, NO2, F, OH and NH2 furnishing 25 examples of substituted aryl ketones in isolated yields of up to 96% in 24 h. Beside the high purity, the ease and convenience of the isolation compared to boronic acids, sodium aryl trihydroxyborate salts could be used subsequently without the addition of excess amount of an activator and are more user-friendly in terms of the use of accurate reaction stoichiometry.

Experimental Evaluation of (L)Au Electron-Donor Ability in Cationic Gold Carbene Complexes

29Si NMR spectroscopy was employed to evaluate the electron donor properties of the (L)Au fragments in the cationic gold (β,β-disilyl)vinylidene complexes [(L)Au=C=CSi(Me)2CH2CH2Si(Me)2]+B(C6F5)4? [L=P(tBu)2o-biphenyl or NHC] relative to the p-substituted aryl group in the α-aryl-(β,β-disilyl)vinyl cations [(p-C6H4X)-C= CSi(Me)2CH2CH2Si(Me)2]+B(C6F5)4?. Similarly, 19F NMR was employed to evaluate the σ- and π-electron donor properties of the (L)Au fragments in the neutral gold fluorophenyl complexes (L)Au(C6H4F) and in the cationic (fluorophenyl)methoxycarbene complexes [(L)AuC(OMe)(C6H4F)]+SbF6? [L=P(tBu)2o-biphenyl or IPr] relative to the p-substituted aryl group of the protonated monofluorobenzophenones [(p-C6H4X)(C6H4F)COH]+OTf?. The results of these studies indicate that relative to p-substituted aryl groups, the gold (L)Au fragments [L=P(tBu)2o-biphenyl or NHC] are significantly more inductively electron donating and are comparable π-donors and for this reason, the extent of (L)Au→C1 electron donation in gold carbene complexes appears to exceed that provided by a p-(dimethyamino)phenyl group. Furthermore, the [L=P(tBu)2o-biphenyl]Au fragment is a nominally stronger electron donor than the (IPr)Au fragment, and both are significantly more inductively electron donating than the (PPh3)Au and [P(OMe)3]Au fragments.

Pd/C in Propylene Carbonate: A Sustainable Catalyst–Solvent System for the Carbonylative Suzuki–Miyaura Cross-Coupling Using N-Formylsaccharin as a CO Surrogate

This work documents the first Pd/C-catalyzed carbonylative Suzuki–Miyaura cross-coupling of aryl iodides with N-formylsaccharin as a CO surrogate. In contrast to previous reaction protocols, which make use of toxic and hazardous solvents, the reaction could be advantageously performed in propylene carbonate as an environmentally benign and sustainable polar aprotic solvent. A range of biaryl ketones, including (4-methoxyphenyl)(3,4,5-trimethoxyphenyl)methanone, an antineoplastic belonging to the phenstatin family, could be synthesized under cocatalyst-free, additive-free and ligand-free conditions. The Pd/C could be recycled up to five times under CO surrogacy with only a marginal decrease in catalytic activity. The reaction could also be scaled up to gram-scale syntheses.

Synthesis and biological evaluation of negative allosteric modulators of the Kv11.1(hERG) channel

We synthesized and evaluated a series of compounds for their allosteric modulation at the Kv11.1 (hERG) channel. Most compounds were negative allosteric modulators of [3H]dofetilide binding to the channel, in particular 7f, 7h-j and 7p. Compounds 7f and 7p were the most potent negative allosteric modulators amongst all ligands, significantly increasing the dissociation rate of dofetilide in the radioligand kinetic binding assay, while remarkably reducing the affinities of dofetilide and astemizole in a competitive displacement assay. Additionally, both 7f and 7p displayed peculiar displacement characteristics with Hill coefficients significantly distinct from unity as shown by e.g., dofetilide, further indicative of their allosteric effects on dofetilide binding. Our findings in this investigation yielded several promising negative allosteric modulators for future functional and clinical research with respect to their antiarrhythmic propensities, either alone or in combination with known Kv11.1 blockers.

Transition-metal-free, ambient-pressure carbonylative cross-coupling reactions of aryl halides with potassium aryltrifluoroborates

We disclose an unprecedented transition-metal-free carbonylative cross coupling of aryl halides with potassium aryl trifluoroborates even at atmospheric pressure of carbon monoxide. This protocol is efficient, operationally simple, and shows wide scope with regard to both aryl halides and potassium aryl trifluoroborates containing a series of active functional groups.

Synthesis and biological evaluation of XB-1 analogues as novel histamine H3 receptor antagonists and neuroprotective agents

A novel class of H3 receptor antagonists, XB-1 analogues based on benzophenone or oxydibenzene scaffolds were synthesized, and their biological activities were evaluated to determine their in vitro neuroprotective effects against Aβ25-35-induced damage in primary cortical neurons and against glutamate-induced neuronal injury in primary cerebellar granule neurons. The results indicated that all of the tested analogues displayed neuroprotective activity at 0.1 μM or 1 μM. These findings may provide new insights into the development of novel promising H3 receptor antagonists with potential neuroprotective activity.

One-pot synthesis of diarylmethanones through palladium-catalyzed sequential coupling and aerobic oxidation of aryl bromides with acetophenone as a latent carbonyl donor

A one-pot palladium-catalyzed synthesis of symmetrical and unsymmetrical diarylmethanones using acetophenone and aryl bromides as raw materials has been developed. In this reaction, acetophenone acts as a latent carbonyl donor and two pathways of palladium-catalyzed sequential coupling and aerobic oxidation are identified. The reaction is applicable to a spectrum of substrates and delivers the products in moderate to good yields. This method can be used for the synthesis of ketoprofen, a nonsteroidal anti-inflammatory drug, in a two-step procedure and 45% overall yield.

Successful application of indirect electrooxidation for the transformation of biaryl methanols to the corresponding biaryl ketones

Various biaryl methanols were electrooxidized into the corresponding biaryl ketones in good yields and under very mild reaction conditions. Because of the relatively high oxidation potential, bulky structure, and somewhat poor solubility, biaryl methanols do not readily undergo direct electrooxidative transformations as a synthetic step toward the corresponding biaryl ketones. Herein, we report the successful indirect electrooxidation of secondary biaryl methanols featuring the use of a slight excess amount of KI (1.2 equivalents, relative to the substrate) in MeOH. Copyright

Synthesis and structure-activity relationship for new series of 4-phenoxyquinoline derivatives as specific inhibitors of platelet-derived growth factor receptor tyrosine kinase

We discovered a new series of 4-phenoxyquinoline derivatives as potent and selective inhibitors of the platelet-derived growth factor receptor (PDGFr) tyrosine kinase. We researched the highly potent and selective inhibitors on the basis of both PDGFr and epidermal growth factor receptor (EGFr) inhibitory activity. First, we found a compound, Ki6783 (1), which inhibited PDGFr autophosphorylation at 0.13 μM, but it did not inhibit EGFr autophosphorylation at 100 μM. After extensive explorations, we found the two desired compounds, Ki6896 (2) and Ki6945 (3), which are substituted by benzoyl and benzamide at the 4-position of the phenoxy group on 4-phenoxyquinoline, respectively. These inhibitory activities were 0.31 and 0.050 μM, respectively, but neither of them inhibited EGFr autophosphorylation at 100 μM. We further investigated the profile of both compounds toward various tyrosine and serine/threonine kinases. The three compounds specifically inhibited PDGFr rather than the other kinases.