Category: 13808-65-6

Milner, Phillip J.; Yang, Yang; Buchwald, Stephen L. published the artcile< In-Depth Assessment of the Palladium-Catalyzed Fluorination of Five-Membered Heteroaryl Bromides>, Safety of 4-Bromo-3-phenyl-1H-pyrazole, the main research area is palladium catalyzed fluorination five membered heteroaryl bromide; bromoazole palladium catalyzed fluorination theor.

A thorough investigation of the challenging Pd-catalyzed fluorination of five-membered heteroaryl bromides is presented. Crystallog. studies and d. functional theory (DFT) calculations suggest that the challenging step of this transformation is C-F reductive elimination of five-membered heteroaryl fluorides from Pd(II) complexes. On the basis of these studies, we have found that various heteroaryl bromides bearing Ph groups in the ortho position can be effectively fluorinated under catalytic conditions. Highly activated 2-bromoazoles, such as 8-bromocaffeine, are also viable substrates for this reaction.

Organometallics published new progress about Crystal structure. 13808-65-6 belongs to class pyrazoles-derivatives, and the molecular formula is C9H7BrN2, Safety of 4-Bromo-3-phenyl-1H-pyrazole.

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Petzold, Daniel; Koenig, Burkhard published the artcile< Photocatalytic Oxidative Bromination of Electron-Rich Arenes and Heteroarenes by Anthraquinone>, Name: 4-Bromo-3-phenyl-1H-pyrazole, the main research area is arene heteroarene oxidative bromination photocatalyst sodium anthraquinonesulfonate.

The estimated excited oxidation potential of sodium anthraquinone-2-sulfonate (SAS) increases from 1.8 V to ∼2.3 V vs. SCE by protonation with Bronsted acids. This increased photooxidation power of protonated anthraquinone was used for the regio-selective oxidative bromination of electron rich (hetero)arenes and drugs in good yield. The mild reaction conditions are compatible with many functional groups, such as double and triple bonds, ketones, amides and amines, hydroxyl groups, carboxylic acids and carbamates. Mechanistic studies indicate the photooxidation of the arene followed by nucleophilic bromide addition as the likely pathway.

Advanced Synthesis & Catalysis published new progress about Aromatic hydrocarbons Role: RCT (Reactant), RACT (Reactant or Reagent). 13808-65-6 belongs to class pyrazoles-derivatives, and the molecular formula is C9H7BrN2, Name: 4-Bromo-3-phenyl-1H-pyrazole.

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Olsen, Kathryn L.; Jensen, Matthew R.; MacKay, James A. published the artcile< A mild halogenation of pyrazoles using sodium halide salts and Oxone>, Name: 4-Bromo-3-phenyl-1H-pyrazole, the main research area is pyrazole halogenation sodium halide oxone green chem.

A mild, inexpensive, and operationally simple pyrazole halogenation method utilizing Oxone and sodium halide salts is reported. This work documents 17 examples of alkyl, aryl, allyl, and benzyl substituted 4-chloro and 4-bromopyrazoles, obtained in up to 93% yield. Reactions are performed in water under ambient conditions and generation of organic byproducts is avoided.

Tetrahedron Letters published new progress about Alkali metal halides, sodium halides Role: RGT (Reagent), RACT (Reactant or Reagent). 13808-65-6 belongs to class pyrazoles-derivatives, and the molecular formula is C9H7BrN2, Name: 4-Bromo-3-phenyl-1H-pyrazole.

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Osawa, Akio; Kaiho, Terumitsu; Ito, Takashi; Okada, Mamiko; Kawabata, Chikako; Yamaguchi, Kentaro; Igeta, Hiroshi published the artcile< Reactions of N-aminopyrazoles with halogenating reagents and synthesis of 1,2,3-triazines>, Product Details of C9H7BrN2, the main research area is triazine; pyrazolamine reaction halogenating agent; ring expansion aminopyrazole.

Reactions of N-aminopyrazoles with halogenating reagents (Cl2, Br2, I2, BrCl, ICl, IBr, N-chlorosuccinimide, and N-bromosuccinimide) were examined Some of these reagents preferentially leas to oxidation of the amino group to give the corresponding 1,2,3-triazines as major products, while others mainly gave either or both of 1-amino-4-halopyrazoles and 5-halo-1,2,3-triazines as the result of halogenation of the 4-position of the pyrazole ring prior to the oxidation of the amino group. In some cases, the oxidation of the amino group and the halogenation of the pyrazole ring proceeded concurrently to form not only the unhalogenated triazines but also the 1-amino-4-halopyrazines and the 5-halotriazines. Various reagents and reaction conditions were explored to utilize the reaction for the synthesis of halogenated and unhalogenated 1,2,3-triazines.

Chemical & Pharmaceutical Bulletin published new progress about Halogenation. 13808-65-6 belongs to class pyrazoles-derivatives, and the molecular formula is C9H7BrN2, Product Details of C9H7BrN2.

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Foces-Foces, Concepcion; Alkorta, Ibon; Elguero, Jose published the artcile< Supramolecular structure of 1H-pyrazoles in the solid state: a crystallographic and ab initio study>, Formula: C9H7BrN2, the main research area is pyrazole derivative supramol structure solid state ab initio.

The secondary structure of 1H-unsubstituted pyrazole derivatives bearing only one hydrogen-donor group and one or more acceptor groups has been analyzed in terms of some descriptors representing the substituents at C3 and C5. The substituent at C4 appears to affect mainly the tertiary or quaternary structure of these compounds The proposed semi-quant. model, which explains most hydrogen-bonded motifs as a combination of the effects of substituents at C3 and C5, has also been examined as a function of the steric and polarizability effects of these substituents represented by molar refractivity. The model also applies to other five-membered rings (1,2,4-triazoles, 1,2,4-diazaphospholes and 1,2,4-diazaarsoles). Furthermore, ab initio calculations at RHF/6-31G* have been performed to discover the relative stability of three of the four hydrogen-bond patterns displayed by several sym. pyrazoles (dimers, trimers, tetramers). The fourth motif, catemers, has only been discussed geometrically.

Acta Crystallographica, Section B: Structural Science published new progress about Density functional theory. 13808-65-6 belongs to class pyrazoles-derivatives, and the molecular formula is C9H7BrN2, Formula: C9H7BrN2.

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Rai, Ganesha; Brimacombe, Kyle R.; Mott, Bryan T.; Urban, Daniel J.; Hu, Xin; Yang, Shyh-Ming; Lee, Tobie D.; Cheff, Dorian M.; Kouznetsova, Jennifer; Benavides, Gloria A.; Pohida, Katie; Kuenstner, Eric J.; Luci, Diane K.; Lukacs, Christine M.; Davies, Douglas R.; Dranow, David M.; Zhu, Hu; Sulikowski, Gary; Moore, William J.; Stott, Gordon M.; Flint, Andrew J.; Hall, Matthew D.; Darley-Usmar, Victor M.; Neckers, Leonard M.; Dang, Chi V.; Waterson, Alex G.; Simeonov, Anton; Jadhav, Ajit; Maloney, David J. published the artcile< Discovery and Optimization of Potent, Cell-Active Pyrazole-Based Inhibitors of Lactate Dehydrogenase (LDH)>, Category: pyrazoles-derivatives, the main research area is pyrazole preparation lactate dehydrogenase inhibitor.

The authors report the discovery and medicinal chem. optimization of a novel series of pyrazole-based inhibitors of human lactate dehydrogenase (LDH). Utilization of a quant. high-throughput screening paradigm facilitated hit identification, while structure-based design and multiparameter optimization enabled the development of compounds with potent enzymic and cell-based inhibition of LDH enzymic activity. Lead compounds such as 63 exhibit low nM inhibition of both LDHA and LDHB, submicromolar inhibition of lactate production, and inhibition of glycolysis in MiaPaCa2 pancreatic cancer and A673 sarcoma cells. Moreover, robust target engagement of LDHA by lead compounds was demonstrated using the cellular thermal shift assay (CETSA), and drug-target residence time was determined via SPR. Anal. of these data suggests that drug-target residence time (off-rate) may be an important attribute to consider for obtaining potent cell-based inhibition of this cancer metabolism target.

Journal of Medicinal Chemistry published new progress about Antitumor agents. 13808-65-6 belongs to class pyrazoles-derivatives, and the molecular formula is C9H7BrN2, Category: pyrazoles-derivatives.

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 13808-65-6, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 13808-65-6 name is 4-Bromo-3-phenyl-1H-pyrazole, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

[0164] In a microwave tube was placed ethyl 2-bromothiazole-4-carboxylate (1058 mg, 4.48 mmol), 3-bromo-4-phenyl-1H-pyrrole (995 mg, 4.48 mmol), and K2C03 (929 mg, 6.72 mmol). The tube was sealed and DMSO (4 ml) was added. The mixture was heated at 120C for 4 h. The mixture was poured into vigorously stirred H20 (100 mL), and the solid was filtered, triturated with H20, and dried. The solid was re-dissolved in EtOAc and filtered. Some undissolved material was the hydrolized acid. The filtrate was concentrated and triturated with ca. 3% EtOAc/hexane to give ethyl 2-(4-bromo-3-phenyl- 1H-pyrazol- 1- yl)thiazole-4-carboxylate (1329 mg, 3.51 mmol, 78% yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-3-phenyl-1H-pyrazole, and friends who are interested can also refer to it.

Reference:
Patent; THE UNITED STATES OF AMERICA AS REPRESENTED BY THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES; VANDERBILT UNIVERSITY; MALONEY, David J.; JADHAV, Ajit; BANTUKALLU, Ganesha Rai; BRIMACOMBE, Kyle Ryan; MOTT, Bryan T.; YANG, Shyh Ming; URBAN, Daniel Jason; HU, Xin; SIMEONOV, Anton; KOUZNETSOVA, Jennifer L.; WATERSON, Alex Gregory; SULIKOWSKI, Gary Allen; KIM, Kwangho; CHRISTOV, Plamen; JANA, Somnath; (387 pag.)WO2016/109559; (2016); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 13808-65-6,Some common heterocyclic compound, 13808-65-6, name is 4-Bromo-3-phenyl-1H-pyrazole, molecular formula is C9H7BrN2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Reference Example 1114-Bromo-3-phenyl-1-trityl-1H-pyrazole A suspension of 4-bromo-3-phenyl-1H-pyrazole (6.13 g, 27.5 mmol), trityl chloride (15.3 g, 55.0 mmol), and K2CO3 (11.4 g, 82.5 mmol) in DMF (100 mL) was stirred for 60 h at 90 C. After cooling to room temperature, the reaction mixture was poured into water and extracted with AcOEt. The extract was washed with water and brine, dried over MgSO4, concentrated under reduced pressure. The residue was recrystallized from hexane/THF to give the title compound (8.00 g, 63% yield) as a white solid: mp 181-183 C.; 1H NMR (300 MHz, CDCl3): delta ppm 7.16-7.22 (6H, m), 7.28-7.41 (13H, m), 7.87-7.91 (2H, m). Anal. Calcd for C28H21BrN2: C, 72.26; H, 4.55; N, 6.02. Found: C, 72.43; H, 4.66; N, 5.91.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-3-phenyl-1H-pyrazole, its application will become more common.

Electric Literature of 13808-65-6, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 13808-65-6 name is 4-Bromo-3-phenyl-1H-pyrazole, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

[0164] In a microwave tube was placed ethyl 2-bromothiazole-4-carboxylate (1058 mg, 4.48 mmol), 3-bromo-4-phenyl-1H-pyrrole (995 mg, 4.48 mmol), and K2C03 (929 mg, 6.72 mmol). The tube was sealed and DMSO (4 ml) was added. The mixture was heated at 120C for 4 h. The mixture was poured into vigorously stirred H20 (100 mL), and the solid was filtered, triturated with H20, and dried. The solid was re-dissolved in EtOAc and filtered. Some undissolved material was the hydrolized acid. The filtrate was concentrated and triturated with ca. 3% EtOAc/hexane to give ethyl 2-(4-bromo-3-phenyl- 1H-pyrazol- 1- yl)thiazole-4-carboxylate (1329 mg, 3.51 mmol, 78% yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-3-phenyl-1H-pyrazole, and friends who are interested can also refer to it.