Category: pyridine-derivatives

69045-84-7, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 69045-84-7, name is 2,3-Dichloro-5-(trifluoromethyl)pyridine. A new synthetic method of this compound is introduced below.

(R) -2- (4-hydroxyphenoxy) propionic acid (3 g),DMF (35 ml), slowly adding K2CO3 (4.55 g),Heating up to 70 ~ 80 ,Stir for 1h,Was added dropwise 2,3-dichloro-5-trifluoromethylpyridine (3.56 g)Keep at 70 ~ 80 for 8h,Stop the reaction,Naturally cooled to room temperature,The mixture was poured into ice water (200 mL)The pH was adjusted to 4 to 5 using dilute hydrochloric acid, extracted with ethyl acetate,Organic phase washed,dry,(R) -2- [4- (5-trifluoromethyl-3-chloropyridin-2-yloxy) phenoxy]Propionic acid brown liquid 5.03 g,Yield 84.4%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,69045-84-7, 2,3-Dichloro-5-(trifluoromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; China Three Gorges University; Liu Qixing; Zhou Haifeng; Lu Guoren; Peng Yuqi; (9 pag.)CN106632293; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

5470-18-8 , The common heterocyclic compound, 5470-18-8, name is 2-Chloro-3-nitropyridine, molecular formula is C5H3ClN2O2, 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 3-nitro-2-chloropyridine (4.0 g, 25.2 mmol) in 15 mL 2-methoxyethanol was added methylamine (2.0 M in THF, 32 mL). The reactionwas stirred for 8 hr at 80 C in a sealed tube. After cooling to rt, the reaction mixture was evaporated to afford 15 quantitatively (3.6 g, 23.2 mmol). 1H NMR (500 MHz, CDCl3) delta 8.47 – 8.37 (m, 2H), 8.20 (s, 1H), 6.64 (dd, J = 8.3, 4.4 Hz, 1H), 3.17 (d, J = 4.8 Hz, 3H). 13C NMR (126 MHz, CDCl3) delta 156.0, 153.5, 135.4, 111.7, 28.4. HRMS (ESI+) m/z calcd for C6H8N3O2+ 154.0617, found 154.0610.

According to the analysis of related databases, 5470-18-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Pollock, Julie A.; Kim, Sung Hoon; Katzenellenbogen, John A.; Tetrahedron Letters; vol. 56; 44; (2015); p. 6097 – 6099;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

The common heterocyclic compound, 151213-42-2, name is (4aR,7aR)-Octahydro-1H-pyrrolo[3,4-b]pyridine, molecular formula is C7H14N2, 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. 151213-42-2

General procedure: A mixture of 6-chloro-4-cyclopropyl-7-fluoro-1-oxo-1,4-dihydronaphthalene-2-carboxylic acid 1a (1 g, 3.5 mmol) with N-ethylpiperazine 2c (0.6 g, 5.25mmol) was loaded in a small flask fitted with a micro condenser, placed in the microwave reactor and irradiated for 25 min at 150C under solvent free conditions. The reaction progress was monitored by TLC. Upon completion of the process, addition of hot absolute ethanol (10 mL) to the reaction mixture was followed by filtration. The filtrate was concentrated and stored at room temperature for precipitation. The solid was filtered off and recrystallized from absolute ethanol to give compound 3c.

The synthetic route of 151213-42-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mirzaie; Lari; Vahedi; Hakimi; Russian Journal of General Chemistry; vol. 86; 12; (2016); p. 2865 – 2869; Zh. Obshch. Khim.; vol. 86; 12; (2016); p. 2865 – 2869,5;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Some common heterocyclic compound, 626-55-1, molecular formula is C5H4BrN, 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.626-55-1

Stage 1Methylpyridin-3-ylamine An amount of 100.1 g (633 mmol) of 3-bromopyridine was stirred with 160 ml (1280 mmol) of 8M methylamine in ethanol, 4 g (27.5 mmol) of 8-hydroxyquinoline and 2.2 g (11.5 mmol) of copper(I) iodide in an autoclave at 120 for 16 hours. The mixture was filtered with suction over sand/silica gel and concentrated, aqueous citric acid and cyclohexane were added to the residue, the aqueous phase was saturated with sodium chloride, admixed with dilute aqueous sodium hydroxide solution to a pH of 10 and extracted 6 times with ethyl acetate, and the combined organic phases were dried over MgSO4 and evaporated. The residue was distilled in a bulb tube under a membrane pump vacuum.Yield: 46.8 g (63% of theory), 1H-NMR (CD3CN) 2.75 (s, 3H), 4.3 (br, 1H), 6.85 (m, 1H), 7.05 (m, 1H), 7.8 (m, 1H), 7.95 (m, 1H)

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 626-55-1.

Reference:
Patent; BAYER CROPSCIENCE AG; US2010/305124; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 18368-63-3, 2-Chloro-6-methylpyridine, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, 18368-63-3, blongs to pyridine-derivatives compound. 18368-63-3

1, 1-dimethylethyl (6-methyl-2-Dyridinyl)acetateTo a stirred solution of tert-butyl acetate (1.013 mL, 7.50 mmol), 2-chloro-6-methylpyridine (638 mg, 5 mmol), chloro(2-di-t-butylphosphino-2′,4′,6′-tri-/’-propyl-1 , 1 ‘-biphenyl)[2-(2- aminoethyl)phenyl]palladium(ll) (34.3 mg, 0.050 mmol) in Toluene (10 mL) at 0 C in a 100-mL round bottom flask under N2 was added a solution of LHMDS (1 M in toluene) (15.00 mL, 15.00 mmol) pre-cooled to 0 C. The reaction was stirred for 30 minutes. LCMS indicated the reaction was complete, so it was poured into ammonium chloride (aqueous, saturated) and water (1 :1 , 40 mL), and extracted with ethyl acetate (3 x 100 mL). The combined organics were dried over sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography (0-25% EtOAc in hexanes) to afford 1 , 1 -dimethylethyl (6-methyl-2-pyridinyl)acetate (918 mg, 4.43 mmol, 89 % yield) as a yellow oil. LC-MS(ES) m/z = 208 [M+H]+. 1 H NMR (400 MHz, DMSO-d6) delta ppm 1.41 (s, 9 H), 2.44 (s, 3 H), 3.68 (s, 1 H), 7.12 (t, J=7.33 Hz, 2 H), 7.64 (t, J=7.71 Hz, 1 H).

With the rapid development of chemical substances, we look forward to future research findings about 18368-63-3.

Reference:
Patent; GLAXOSMITHKLINE LLC; AXTEN, Jeffrey, Michael; GRANT, Seth, Wilson; HEERDING, Dirk, A.; MEDINA, Jesus, Raul; ROMERIL, Stuart, Paul; TANG, Jun; WO2011/119663; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

626-64-2, 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 626-64-2, name is Pyridin-4-ol. This compound has unique chemical properties. The synthetic route is as follows.

9.5 g (0.10 mol) of 4-hydroxypyridine,, 21.5 g (0.11 mol) of 4-bromobutyric acid ethyl ester,0.5 g of 5% Pd / C catalyst,80 ml of ethanol was placed in a 300 ml autoclave, and the interior of the container was replaced with hydrogen.While introducing hydrogen gas into the vessel, the reactor was heated to 100 C. while stirring, and the reaction was carried out at a hydrogen pressure of 4.9 ¡Á 10 5 Pa for 9 hours.After allowing the reactor to cool down, disappearance of 4-hydroxypyridine was confirmed by TLC. The catalyst was removed by filtration, and the obtained reaction solution was concentrated.To the residue was added 100 ml of water and extracted with 60 ml of ethyl acetate, and the organic layer was dried and concentrated. After drying the obtained solid under reduced pressure, 18.3 g (85 mmol, yield 85%) of (4-hydroxy) -4-piperidinobutanoic acid ethyl ester was obtained.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 626-64-2, Pyridin-4-ol.

Reference:
Patent; TOKUYAMA CORPORATION; SEKI, MASAHIKO; YAMAMOTO, HIROMASA; (13 pag.)JP2018/24593; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.13534-99-1, name is 2-Amino-3-bromopyridine, molecular formula is C5H5BrN2, molecular weight is 173.01, as common compound, the synthetic route is as follows.13534-99-1

equipped with a mechanical stirring three 500mL flask, 30g2- amino-3-bromo-pyridine, 52.8 g as an associated boronic acid pinacol ester, 300mL1,4- dioxane, 4.2gPd (dppf)2Cl2, 59.3g of anhydrous potassium acetate, purged with nitrogen three times, heated to about 80 open overnight.TLC the reaction was complete, cooling, filtration, the filter cake washed twice with 30mL dichloromethane and the filtrate was concentrated to dryness, 200mL of methanol and 20g active carbon was stirred at room temperature overnight, filtration.Concentrated to dryness to give an oil, and petroleum ether was added 15mL 200mL MTBE heating overnight, filtered to give 28g2-amino-4-boronic acid pinacol ester in a yield of 72.8%.

Statistics shows that 13534-99-1 is playing an increasingly important role. we look forward to future research findings about 2-Amino-3-bromopyridine.

Reference:
Patent; Shanghai Rainbow Chemistry Co.,Ltd; Wu, Gang; Yan, taotao; Wei, xianli; (13 pag.)CN102786543; (2016); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

504-29-0 , The common heterocyclic compound, 504-29-0, name is Pyridin-2-amine, molecular formula is C5H6N2, 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.

75.2 g (0.80 mol) Of 2-aminopyridine was dissolved in 88.0 g (0.88 mol) of ethyl acrylate and 20 mL of acetic acid. The mixture was heated to 80C and stirred for 24 hours at the same temperature. -Solvent was removed under vacuum, and the title compound was isolated by vacuum distillation to obtain 77.0 g of ethyl 3-(2- pyridylamino)propionate as a white solid.Yield: 77.Og (49.67%); Purity by HPLC: 98.5%.

According to the analysis of related databases, 504-29-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MEGAFINE PHARMA (P) LTD.; MATHAD, Vijayavitthal Thippannachar; SOLANKI, Pavankumar Vrajlal; UPPELLI, Sekhar Babu; SARODE, Ganesh Gitaram; WO2015/128875; (2015); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

115473-15-9, Adding a certain compound to certain chemical reactions, such as: 115473-15-9, 5,6,7,7a-Tetrahydrothieno[3,2-c]pyridin-2(4H)-one hydrochloride, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, 115473-15-9, blongs to pyridine-derivatives compound.

To a reaction flask equipped with a stirrer, a condenser and a thermometer was added 19.2 g of 5,6,7,7a-tetrahydrothieno[3,2-c]pyridin-2(4H)-one, which was then dispersed in 80 mL dichloromethane and cooled to 0 C. under stirring. 30.4 g of triethylamine were added to the mixture. After addition of 15.2 g of 3-cyanobenzyl bromide to the reaction system in batches, the reaction mixture was heated to reflux and continued to react for 5 h (completion of the reaction was monitored by TLC). The reaction liquid was washed with water (3¡Á80 mL). Then the dichloromethane layer was separated, fully dried over anhydrous sodium sulfate, and filtered. The dichloromethane was evaporated off under reduced pressure to obtain 20.8 g light yellow solid product (HPLC: 96.4%). Rf=0.45 [single point, developing solvent: v (petroleum ether): v (ethyl acetate)=1:2]. MS, m/Z: 270.0 (M).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,115473-15-9, its application will become more common.

Reference:
Patent; TIANJIN INSTITUTE OF PHARMACEUTICAL RESEARCH; LIU, Dengke; LIU, Ying; YUE, Nan; CHEN, Furong; TAN, Chubing; ZHOU, Yunsong; LIU, Peng; ZHAO, Yigui; ZHI, Deguang; LIU, Mo; LIU, Bingni; HUANG, Changjiang; TANG, Lida; US2013/72521; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding some certain compound to certain chemical reactions, such as: 16013-85-7, name is 2,6-Dichloro-3-nitropyridine, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 16013-85-7. 16013-85-7

Prior synthesis of pyrido[3,2-d]pyrimidines utilized ethoxyethanol and aniline for substitution on 3 (Scheme 1) whereas for substituted anilines, strong bases such as LDA were used to facilitate the reaction. Both methods suffer from long durations and stringent reaction conditions, respectively. A simpler and versatile synthetic route to obtain 4-18 from 3 was envisioned using appropriate anilines at reflux in isopropanol at 120 C, a highly versatile reaction process that provided good yields (75-83%). Reduction of the nitro group was performed using iron in cone. HCl (Bechamp reduction) or using H2/Pd to give quantitative yields. Cyclization of the resultant intermediate with chlorformamidine in dimethylsulfone at 140 C provided the desired target compounds.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 16013-85-7.

Reference:
Patent; DUQUESNE UNIVERSITY OF THE HOLY SPIRIT; GANGJEE, Aleem; (140 pag.)WO2017/31176; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem