Category: pyridine-derivatives

Reference of 78686-77-8, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 78686-77-8 as follows.

Example 38 – Preparation of Intermediate 13 [ 00277 ] The synthesis of Intermediate 13 followed General Procedure 11 following: General Procedure 11 Intermediate 12 Intermediate 13 [ 00278 ] To a cold (0C) solution of 3-(5-amino-lH-pyrazol-3-yl) pyridine- 2(lH)-one (Intermediate 11, 9.0 g, 0.036 mol, 1 eq) in methanol (25 mL) was added sodium methoxide (25% in methanol, 15.5 mL, 0.072 mol, 2 eq). The reaction was stirred for 2 hours at room temperature. After completion of reaction, the reaction mixture was evaporated under reduced pressure, and the residue was poured into ice cold water under stirring. This mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulpfate and concentrated under reduced pressure. The residue was purified by column chromatography using neutral silica gel, eluting with 25-30% ethyl acetate in hexane to give pure desired product (7.5 g, yield-84.74%>) m/z[M+H]+ 246.17 1H NMR (DMSO-d6, 400 MHz) delta 8.73 (d, J = 1.5 Hz, 1H), 8.41 (d, J= 1.5 Hz, 1H), 4.02 (d, J= 1.1 Hz, 3H), 3.86 (d, J= 1.1 Hz, 3H) ppm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,78686-77-8, its application will become more common.

Reference:
Patent; VERSEON CORPORATION; SHORT, Kevin Michael; KITA, David Ben; ESTIARTE-MARTINEZ, Maria de los Angeles; PHAM, Son Minh; (244 pag.)WO2016/44662; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1159812-31-3, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 1159812-31-3, name is 7-Bromo-2-methyl-[1,2,4]triazolo[1,5-a]pyridine. This compound has unique chemical properties. The synthetic route is as follows.

To boronic acid ester compound having triazole side chain (23, 2.63 g) and 7-bromotriazolopyridine derivative (24, 2.15 g, prepared as described in Example 4 using compound 18 of Example 5) in dioxane (50 mL) and water (12 mL), Na2CO3 (2.47 g) and Pd(Ph3P)4 (821 mg) were added and the reaction mixture was heated at 90 C. to 100 C. for 1.5 hours. The solvent was then removed under reduced pressure to reduce the volume by half, and water was added. After the resulting precipitate was filtered and dissolved in ethanol, 1.95 g of colorless compound 25 was precipitated (73%).Compound 25: 1H-NMR (300 MHz, DMSO-d6) 2.48 (br s, 3H), 3.96 (dd, 9.5, 6, 1H), 4.30 (dd, 9.5, 9.5, 1H), 4.86 (d, 5, 2H), 5.19 (ddt, 9.5, 6, 5, 1H), 7.30 (ddd, 7, 1.5, 1.5, 1H), 7.42 (dd, 8.5, 2, 1H), 7.58 (dd, 14, 2, 1H), 7.74 (dd, 8.5, 8.5, 1H), 7.77 (d, 1, 1H), 7.86 (br s, 1H), 8.18 (d, 1, 1H), 8.88 (d, 7, 1H);LRMS m/z 393 (M+, 7), 349 (14), 320 (6), 279 (8), 242 (10), 158 (11), 108 (21), 80 (29), 53 (100).

According to the analysis of related databases, 1159812-31-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Katoh, Issei; Aoki, Toshiaki; Suzuki, Hideyuki; Utsunomiya, Iwao; Kuroda, Norikazu; Iwaki, Tsutomu; US2011/98471; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1256808-59-9 , The common heterocyclic compound, 1256808-59-9, name is 5-Fluoro-3-methylpicolinic acid, molecular formula is C7H6FNO2, its 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.

To a solution of tert-butyl ((3aS,4R,8R)-4-(6-amino-3-fluoropyridin-2-yl)-4,7,7- trimethyl-8-oxido-3,3a,4,7-tetrahydro-2H-isothiazolo[l,5-a][l,4]thiazin-6-yl)carbamate (Int- 39AB, 150 mg, 0.35 mmol) in THF (20 mL) was added 5-fluoro-3-methylpicolinic acid (82 mg, 0.53 mmol) followed by T3P (1.1 g, 1.75 mmol, 50% in ethyl acetate), and diisopropylethylamine (267 mg, 2.1 mmol). The reaction was stirred at 70 C for 4 h. After that, the reaction mixture was diluted with aqueous saturated sodium hydrogencarbonate solution (20 mL) and extracted with ethyl acetate (3 x 30 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated to give a crude product. The crude was purified by column chromatography (silica gel, eluting with petroleum ether / ethyl acetate 1: 1) to yield, after drying in vacuo, the title compound as a yellow solid (130 mg, 66% yield). XH NMR (CDC13, 400 MHz): delta 1.50-1.59 (m, 1 H), 1.66 (s, 9 H), 1.86 (s, 3 H), 1.97 (s, 3 H), 2.06-2.12 (m, 1 H), 2.14 (s, 3 H), 2.84 (s, 3 H), 3.54 (dd, J = 7.7, 10.7 Hz, 1 H), 3.69 (ddd, J = 4.8, 10.7, 10.7 Hz, 1 H), 4.30 (ddd, / = 2.1, 7.1, 12.0 Hz, 1 H), 7.40 (dd, J = 2.1, 8.9 Hz, 1 H), 7.58 (dd, = 9.1, 10.0 Hz, 1 H), 8.31 (d, J = 2.6 Hz, 1 H), 8.49 (dd, / = 3.1, 8.9 Hz, 1 H), 10.78 (s, 1 H), 12.54 (s, 1 H). MS (ES+) m/z 563.2 [M+H].

The synthetic route of 1256808-59-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BARTELS, Bjoern; CUENI, Philipp; DOLENTE, Cosimo; GUBA, Wolfgang; HAAP, Wolfgang; KUGLSTATTER, Andreas; OBST SANDER, Ulrike; PETERS, Jens-Uwe; ROGERS-EVANS, Mark; VIFIAN, Walter; WOLTERING, Thomas; (231 pag.)WO2016/55496; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 87674-15-5, 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. 87674-15-5, name is 1-(3-Fluoropyridin-4-yl)ethanol, molecular formula is C7H8FNO, The 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.

A mixture of 1-(3-fluoropyridin-4-yl)ethanol (10 g, 70.3 mmol) and commercial activated MnO2 (8 g, 92.1 mmol) in toluene (100 mL) were refluxed until disappearance of starting material. After cooling, the mixture was filtered on a bed of celite, the cake washed with toluene and the organic phases concentrated to give 3-fluoro-4-acetyl pyridine (6.9 g, 70%) that was used directly in the next step.

According to the analysis of related databases, 87674-15-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pharmacia Italia S.p.A.; US2007/142415; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 72093-04-0, name is 3-Chloro-4-methylpyridine, the common compound, a new synthetic route is introduced below. Recommanded Product: 72093-04-0

To a solution of lithium diisopropylamide (6mL, 2M in THF, l2mmol) in 5mL THF at -70C was added under argon a solution of 3-chloro-4-methylpyridine (1 .28g, leq, 1 Ommol) in 5mL THF. The mixture was stirred for 5mm at -70C and then allowed to reach -3 0C. Thereafter the mixture was cooled down to – 70C and a solution of 1-chloro-3,3-dimethylbutan-2-one (2.7g. 2eq, 2Ommol) in 5mL THF was added. Then the mixture was allowed to reach ambient temperature and stirred for lh. Thereafter the mixture wascooled to 0C and saturated aqueous ammonium chloride solution was added. After extraction with ethyl acetate and evaporation of the solvent the cmde material was purified via column chromatography over silica gel (eluent cyclohexane ethyl acetate gradient). After evaporation of the solvent 2g (8 1%) of 4-[(2- tert-butyloxiran-2-yl)methyl]-3-chloropyridine were obtained as colourless oil.MS (ESI): 226.1 ([M+H]+)

The synthetic route of 72093-04-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER CROPSCIENCE AG; HOFFMANN, Sebastian; SUDAU, Alexander; DAHMEN, Peter; WACHENDORFF-NEUMANN, Ulrike; BERNIER, David; BRUNET, Stephane; LACHAISE, Helene; VIDAL, Jacky; GENIX, Pierre; COQUERON, Pierre-Yves; GEIST, Julie; VORS, Jean-Pierre; KENNEL, Philippe; MILLER, Ricarda; WO2014/167010; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Article, Dalton Transactions called Energetic C-trinitromethyl-substituted pyrazoles: synthesis and characterization, Author is Zhang, Yiying; Li, Yanan; Hu, Jianjian; Ge, Zhongxue; Sun, Chenghui; Pang, Siping, which mentions a compound: 948552-36-1, SMILESS is O=CC1=CC=NN1, Molecular C4H4N2O, Quality Control of 1H-Pyrazole-5-carbaldehyde.

A new family of C-trinitromethyl-substituted pyrazoles was designed and obtained in good yields by the reaction of N2O4 with the pyrazolecarbaldehyde oxime followed by further N-nitration and C-nitration. All of the new compounds were fully characterized by IR and NMR spectroscopy, elemental anal. and differential scanning calorimetry (DSC). Compounds 2 and 3 were further confirmed by X-ray crystallog. These pyrazole derivatives have good densities, pos. enthalpies of formation and acceptable sensitivity values. Theor. calculations carried out using Gaussian 03 and EXPLO5 program demonstrate good to excellent detonation velocities and pressures in the range of ADN and HMX. Compound 3 exhibiting a pos. oxygen balance, high specific impulse and moderate thermal stability is a promising high energy d. oxidizer.

This compound(1H-Pyrazole-5-carbaldehyde)Quality Control of 1H-Pyrazole-5-carbaldehyde was discussed at the molecular level, the effects of temperature and reaction time on the properties of the compound were discussed, and the optimum reaction conditions were selected.

Reference:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Pfeifer, David; Russegger, Andreas; Klimant, Ingo; Borisov, Sergey M. published the article 《Green to red emitting BODIPY dyes for fluorescent sensing and imaging of carbon dioxide》. Keywords: dipyrrometheneboron difluoride preparation fluorescent imaging emitting carbon dioxide sensor.They researched the compound: 2,4-Dimethyl-1H-pyrrole( cas:625-82-1 ).COA of Formula: C6H9N. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:625-82-1) here.

Several new BODIPY pH indicators are prepared and tested as transducers in polymer-based optical carbon dioxide sensors. Apart from classical BODIPY chromophore absorbing at around 505 nm, π-extended analogs showing absorption maxima at around 635 and 665 nm are prepared All the dyes possess excellent brightness due to combination of high molar absorption coefficients and fluorescence quantum yields. Addnl., the π-extended BODIPYs show unmatched photostability whereas the classical 1,3,5,7-tetramethyl-8-aryl-4,4-difluoroboradiazaindacene is found to be photolabile. The phenol receptors render BODIPY dyes pH sensitive inducing fluorescence quenching in the phenolate form. Carbon dioxide sensors are prepared via immobilization of the dyes into Et cellulose along with tetraoctylammonium hydrogencarbonate. The sensitivity of these sensors is mainly guided by the nature of the receptor and to a smaller extent by the nature of the chromophore, and can be tuned over a very wide range covering all important applications. Introduction of the receptor bearing carboxylic group in the o-position towards OH group of the receptor enables highly sensitive sensors resolving ambient CO2 levels (LOD 0.009 hPa). Sensors based on other indicators show optimal response from 0.2 to 60 hPa and from 20 to 400 hPa, making them attractive for medical and food packaging applications, resp. Materials for referenced sensing with phase fluorometry and ratiometric imaging with RGB cameras have also been prepared

This compound(2,4-Dimethyl-1H-pyrrole)COA of Formula: C6H9N was discussed at the molecular level, the effects of temperature and reaction time on the properties of the compound were discussed, and the optimum reaction conditions were selected.

Reference:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Most of the natural products isolated at present are heterocyclic compounds, so heterocyclic compounds occupy an important position in the research of organic chemistry. A compound: 625-82-1, is researched, SMILESS is CC1=CNC(C)=C1, Molecular C6H9NJournal, Article, Research Support, Non-U.S. Gov’t, Angewandte Chemie, International Edition called An Ethacrynic Acid-Brominated BODIPY Photosensitizer (EA-BPS) Construct Enhances the Lethality of Reactive Oxygen Species in Hypoxic Tumor-Targeted Photodynamic Therapy, Author is Won, Miae; Koo, Seyoung; Li, Hao; Sessler, Jonathan L.; Lee, Jin Yong; Sharma, Amit; Kim, Jong Seung, the main research direction is ethacrynic acid brominated BODIPY preparation photosensitizer PDT hypoxic cancer; BODIPY; Hypoxia; ethacrynic acid; glutathione S-transferase-pi; photodynamic therapy.Application of 625-82-1.

Despite being a clin. approved intervention for cancer, photodynamic therapy (PDT) still suffers from limitations. Prime among these is a therapeutic response that is mostly oxygen dependent. This limits the utility of PDT in treating hypoxic tumors since lower levels of cytotoxic reactive oxygen species (ROS) are generated in regions of low oxygen tension. Glutathione-pi (GST-pi) is a key enzyme that militates against ROS-mediated apoptosis. We report herein a new construct, EA-BPS, that contains both a brominated BODIPY photosensitizer (BPS) and an ethacrynic acid (EA) GST-pi inhibitor. Photoirradiation of EA-BPS induces a synergistic antitumor effect that results from the combination of ROS production and GST-pi inhibition. Relative to BPS alone, an enhanced cell-killing effect is seen under hypoxic conditions both in vitro and in vivo. We conclude that by making better use of the available oxygen in tumor environments, improved therapeutic PDT outcomes should be achievable even under hypoxic conditions.

This compound(2,4-Dimethyl-1H-pyrrole)Application of 625-82-1 was discussed at the molecular level, the effects of temperature and reaction time on the properties of the compound were discussed, and the optimum reaction conditions were selected.

Reference:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Product Details of 948552-36-1. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: 1H-Pyrazole-5-carbaldehyde, is researched, Molecular C4H4N2O, CAS is 948552-36-1, about Synthesis of pyrrolo[1,2-c]imidazol-5-one, pyrrolo[1,2-a]imidazol-5-one, and pyrrolo[1,2-b]pyrazol-6-one (three isomeric azapyrrolizinones) by pyrolysis of Meldrum’s acid derivatives. Author is McNab, Hamish.

Reaction of Meldrum’s acid with 4- or 2-imidazolecarboxaldehyde or 3-pyrazolecarboxaldehyde gave condensation products, which were pyrolyzed in the gas phase to give the title aza analogs I-III, resp., of 3-pyrrolizinone, as air-sensitive yellow solids.

This compound(1H-Pyrazole-5-carbaldehyde)Product Details of 948552-36-1 was discussed at the molecular level, the effects of temperature and reaction time on the properties of the compound were discussed, and the optimum reaction conditions were selected.

Reference:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Product Details of 948552-36-1. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: 1H-Pyrazole-5-carbaldehyde, is researched, Molecular C4H4N2O, CAS is 948552-36-1, about Cytotoxic activity of new cerium (III) complexes of bis-coumarins. Author is Kostova, Irena; Manolov, Ilia; Momekov, Georgi; Tzanova, Tzvetomira; Konstantinov, Spiro; Karaivanova, Margarita.

Complexes of Ce (III) with bis-coumarins, 3,3′-benzylidene-bis(4-hydroxy-2H-1-benzopyran-2-one) and bis(4-hydroxy-2-oxo-2H-chromen-3-yl)-(1H-pyrazol-3-yl)methane, were synthesized by reaction of Ce(III) salt and the ligands, in amounts equal to metal/ligand molar ratio of 1:2. The complexes were prepared by adding an aqueous solution of Ce (III) salt to an aqueous solution of the ligand subsequently raising the pH of the mixture gradually to ∼5.0 by adding dilute solution of NaOH. The Ce (III) complexes with bis-coumarins were characterized by different physicochem. methods-elemental anal., IR-, 1H- and 13C-NMR-spectroscopies and mass-spectral data. The spectral data of Ce (III) complexes were interpreted from comparison with the spectra of the free ligands. This anal. showed that in the Ce (III) complexes the ligands coordinated to the metal ion through both deprotonated hydroxyl groups. From the ν(C=O) red shift observed, participation of the carbonyl groups in the coordination to the metal ion was also suggested. Cytotoxic screening by MTT assay was carried out. The authors performed comparative evaluation of the cytotoxic effects of the two newly synthesized Ce complexes against the acute myeloid leukemia derived HL-60 and the chronic myeloid leukemia (CML)-derived BV-173. The cytotoxic effects of Ce (III) complex with 3,3′-benzylidene-bis(4-hydroxy-2H-1-benzopyran-2-one) were evaluated on the CML-derived K-562 and LAMA-84 cells, characterized by relative low responsiveness to chemotherapy. The DNA isolated from the cytosolic fraction of BV-173 cells after 24 h treatment with the same complex (at 100 and 200 μM) demonstrated a laddering phenomenon that is indicative for apoptotic cell death.

This compound(1H-Pyrazole-5-carbaldehyde)Product Details of 948552-36-1 was discussed at the molecular level, the effects of temperature and reaction time on the properties of the compound were discussed, and the optimum reaction conditions were selected.

Reference:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem