Category: pyridine-derivatives

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. 1189513-51-6, name is 5-Bromo-3-chloropicolinic acid, the common compound, a new synthetic route is introduced below. SDS of cas: 1189513-51-6

To a solution of Compound 1 (10 g) in methylene chloride (200 mL) were added oxalyl chloride (4.43 mL) andN,N-dimethylformamide (0.16 mL) at room temperature, and the mixture was stirred at room temperature for 2 hours.The reaction solution was concentrated under reduced pressure, the residue was dissolved in tetrahydrofuran (50 mL),and this was added dropwise to a suspension of thiosemicarbazide (3.85 g) and pyridine (75 mL) under ice cooling over10 minutes. After dropwise addition, the mixture was stirred at room temperature for 2 hours and concentrated underreduced pressure. The residue was dissolved in a 2N aqueous sodium hydroxide solution (210 mL), and heated at refluxfor 16 hours. The reaction solution was ice cooled and neutralized with concentrated hydrochloric acid (35 mL). Thedeposit was collected by filtration and washed with water and methanol. The obtained solid was suspended and washedin diethyl ether (50 mL), collected by filtration and dried at 50 °C under reduced pressure to obtain Compound 2 (9.46g) as a beige solid.MS (m/z): 291/293/295 [M+H]+

The synthetic route of 1189513-51-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Mitsubishi Tanabe Pharma Corporation; SARUTA, Kunio; HAYASHI, Norimitsu; SAKURAI, Osamu; SAWAMOTO, Hiroaki; OBOKI, Eri; EP2862856; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 875781-15-0, 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. 875781-15-0, name is 5-Bromo-2-fluoronicotinaldehyde, molecular formula is C6H3BrFNO, 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 5-bromo-2-fluoro-pyridine-3-carbaldehyde (200.0 mg, 0.980 mmol, 1.0 eq.) and (4-fluorophenyl)hydrazine hydrochloride (159.4 mg 0.980 mmol, 1.0 eq.) in NMP (3.0 mL) was stirred at ambient temperature for two hours, before caesium carbonate (958.3 mg, 2.941 mmol, 3.0 eq.) was added and the mixture was heated to 115 C. for 1 hour. The mixture was cooled to ambient temperature, and was diluted with water/EtOAc. The layers were separated, and the aqueous layer was extracted two more times with EtOAc. The combined organic layers were then washed with brine and were dried over MgSO4. The solvent was removed under reduced pressure and the remains were purified using silica gel chromatography to obtain 184.4 mg (64%) of 5-bromo-1-(4-fluorophenyl)-1H-pyrazolo[3,4-b]pyridine.

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 875781-15-0, 5-Bromo-2-fluoronicotinaldehyde.

Reference:
Patent; Gruenenthal GmbH; JAKOB, Florian; ALEN, Jo; KRUeGER, Sebastian; SCHADE, Markus; FRIEBE, Daniela; HENNEN, Stephanie; US2019/185470; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 14432-12-3, 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. 14432-12-3, name is 4-Amino-2-chloropyridine, molecular formula is C5H5ClN2, 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.

2-Chloro-4-aminopyridine (1.8 g, 14 mmol) was dissolved in 28 ml dimethylformamide. N-Iodosuccinimide (3.15 g, 14 mmol) was added and the mixture was stirred at room temperature overnight. Additional N-iodosuccinimide (3.15 g, 14 mmol) was added and the mixture wasa stirred at 55 ºC overnight. The mixture was evaporated to dryness and the residue was partitioned between ethyl acetate and water. The aqueous was extracted with ethyl acetate and the combined organics were dried over sodium sulphate, filtered and evaporated under reduced pressure. Purification by flash chromatography (ethyl acetate-hexane gradient, 15:85 rising to 25:75) gave 1.5 g (5.9 mmol, 42%) of the title compound as a purple solid. [0369] 1H NMR (300 MHz, CHLOROFORM-d) delta ppm 8.34 (1 H, s), 6.63 (1 H, s), 4.75 (2 H, br. s.).

According to the analysis of related databases, 14432-12-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Almirall, S.A.; Vidal Juan, Bernat; Alonso Diez, Juan Antonio; Buil Albero, Maria Antonia; Eastwood, Paul Robert; Esteve Trias, Cristina; Lozoya Toribio, Maria Estrella; Roberts, Richard Spurring; Vidal Gispert, Laura; EP2548876; (2013); 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. 52833-94-0, name is 2-Amino-5-bromonicotinic acid, the common compound, a new synthetic route is introduced below. Safety of 2-Amino-5-bromonicotinic acid

To a stirred solution of 2-amino-5-bromonicotinic acid (5.0 g, 23.04 mmol) and sodium acetate (3.78 g, 46.1 mmol) in 100 ml_ of 60 % ethanol in water, were added a refluxed solution of sodium acetate (3.78 g, 46.1 mmol) followed by 2-chloro-1 ,1 – dimethoxyethane (5.74 g, 46.1 mmol) in concentrated hydrochloric acid (1 .0 ml_) in water (6 ml_) and the reaction mass was refluxed for 2.5 h. The solvent was removed, residue obtained was diluted with cold water and pH adjusted to neutral (~7) with saturated sodium bicarbonate solution. The reaction mixture was extracted with ethyl acetate (2×100 ml_), washed with water (2×100 ml_) and brine (2×100 ml_) and dried over anhydrous sodium sulphate. The crude material obtained was purified by trituration using 2 % ethyl acetate in petroleum ether. Yield: 4.8 g (86 %); 1 H NMR (DMSO-d6, 300 MHz): delta 7.66 (d, 1 H, J=1 .2 Hz, Ar), 7.79 (d, 1 H, J=1 .5 Hz, Ar), 8.04 (s, 1 H, Ar), 8.96 (d, 1 H, J=1 .5 Hz, Ar); MS (ES+): m/e 242 (M+1 ).

The synthetic route of 52833-94-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PIRAMAL ENTERPRISES LIMITED; SHARMA, Rajiv; GHOSH, Usha; MORE, Tulsidas; KULKARNI, Mahesh; BAJAJ, Komal; BURUDKAR, Sandeep; RIZVI, Zejah; WO2014/80241; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 2002-04-2, 5-(Pyridin-4-yl)-1,3,4-thiadiazol-2-amine, 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, HPLC of Formula: C7H6N4S, blongs to pyridine-derivatives compound. HPLC of Formula: C7H6N4S

General procedure: 2-Amino-5-(4-pyridinyl)-1,3,4-thiadiazole (0.057 g, 0.32 mmol) was mixed with 3,4-dichlorophenyl isocyanate (0.050 g, 0.027 mmol), dissolved in DMF (1 mL), and heated at 90C for 30 min. The mixture was allowed to cool before quenching with DI water (1 mL) to yield a precipitate.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,2002-04-2, 5-(Pyridin-4-yl)-1,3,4-thiadiazol-2-amine, and friends who are interested can also refer to it.

Reference:
Article; Rosenthal, Andrew S.; Dexheimer, Thomas S.; Gileadi, Opher; Nguyen, Giang H.; Chu, Wai Kit; Hickson, Ian D.; Jadhav, Ajit; Simeonov, Anton; Maloney, David J.; Bioorganic and Medicinal Chemistry Letters; vol. 23; 20; (2013); p. 5660 – 5666;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 164666-68-6 ,Some common heterocyclic compound, 164666-68-6, molecular formula is C6H7ClN2, 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 an ice cold solution of 6-chloro-2-methylpyridin-3-amine (12 g, 84 mmol) and AcOH (5.1 g, 84 mmol) in MeOH (198 g, 250 mL) was dropwise added bromine (13.5 g, 84 mmol). The resulting solution was stirred at ice bath temperature overnight after which it was concentrated under vacuo.The obtained residue was dissolved in EtOAc and sequentially washed with saturated aqueous NaHCO3 solution, 10% Na2S2O3 aqueous solution, brine and dried (Na2SO4). The solvent was removed under vacuo and the obtained crude material was purified by flash chromatography to afford 4- bromo-6-chloro-2-methylpyridin-3-amine (12.6 g).?H NMR (500 MHz, Chloroform-d) 6 7.30 (s, 1H), 4.04 (brs, 2H), 2.46 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,164666-68-6, its application will become more common.

Reference:
Patent; H. LUNDBECK A/S; KEHLER, Jan; JUHL, Karsten; MARIGO, Mauro; VITAL, Paulo, Jorge, Vieira; JESSING, Mikkel; LANGGARD, Morten; RASMUSSEN, Lars, Kyhn; CLEMENTSON, Carl, Martin, Sebastian; (278 pag.)WO2019/115567; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1211580-54-9 ,Some common heterocyclic compound, 1211580-54-9, molecular formula is C6H4BrF2N, 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 4-bromo-2-(difluoromethyl)pyridine (2.5 g, 12.02 mmol), ethynyltrimethylsilane (2.5 mL, 18.03 mmol) and triethylamine (8.4 mL, 60.10 mmol) in DMF (30.0 mL) was degassed by bubbling with argon for 30 min treated with Pd(PPh3)2Cl2 (0.42 g, 0.60 mmol) with continued argon bubbling, treated Cul (0.23 g, 1.20 mmol), warmed to 65C overnight. Reaction mixture was cooled to room temperature and partitioned between 1M HC1 and EtOAc. The organic layer was washed with brine, dried over Na2S04, filtered and concentrated. The suspension was concentrated to dryness and the resulting crude product was purified by Teledyne-Isco flash system by using Hexane/EtOAc, 0 to 5% of hexane in ethyl acetate to provide compound 17 as light yellow liquid ( 1.85 g, 69% yield). lH NMR (400 MHz, DMSO-d6) delta (ppm): 8.70 (d, 1H), 7.69 (s, 1H), 7.61 (d, 1H), 7.09-6.81 (m, 1H), 0.26 (s, 9H); MS (ESI): Calcd. for Cl lH13F2NSi: 225, found 226 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1211580-54-9, its application will become more common.

Reference:
Patent; NANTBIO, INC.; TAO, Chunlin; POLAT, Tulay; YU, Chengzhi; (65 pag.)WO2019/5297; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 67346-74-1, 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 67346-74-1 as follows.

Reference Example 1 3-(3-(4-Benzyloxy-benzyl)-isoxazol-5-yl)-pyridin-2-ylamine; To a mixture of 4-benzyloxy-phenyl-acetohydroximoyl chloride (1.2 g, 4.4 mmol) described in Manufacturing Example 1-1-3 and tetrahydrofuran (34 mL) were added 3-Ethynyl-pyridin-2-ylamine (260 mg, 2.2 mmol) described in Manufacturing Example 1-2-3 and triethylamine (3.0 mL, 22 mmol) at 0 C., which was stirred for 1 hour at room temperature. To the reaction mixture was added water at room temperature, which was then extracted with ethyl acetate-tetrahydrofuran (2:1). The organic layer was washed with saturated aqueous sodium chloride, and the solvent was evaporated under a reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate_heptane=1:3) to obtain the title compound (240 mg, 15%).1H-NMR Spectrum (CDCl3) delta (ppm): 4.00 (2H, s), 5.05 (2H, s), 5.41 (2H, s), 6.24 (1H, s), 6.71 (1H, dd, J=4.9, 7.6 Hz), 6.93-6.97 (2H, m), 7.18-7.22 (2H, m), 7.31-7.44 (5H, m), 7.70 (1H, dd, J=1.7, 7.6 Hz), 8.13 (1H, dd, J=1.8, 4.9 Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,67346-74-1, its application will become more common.

Reference:
Patent; Tanaka, Keigo; Yamamoto, Eiichi; Watanabe, Naoaki; US2009/82403; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 171366-19-1 , The common heterocyclic compound, 171366-19-1, name is (2-Fluoro-4-iodopyridin-3-yl)methanol, molecular formula is C6H5FINO, 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.

[00344] 3-(((tert-Butyldimethylsilyl)oxy)methyl)-2-fluoro-4-iodopyridineTo a solution of (2-fluoro-4-iodopyridin-3-yl)methanol (3.52 g, 13.91 mmol) in CH2CI2 (80 mL) at room temperature was sequentially added imidazole (1.894 g, 27.8 mmol) and TBDMS-C1 (2.52 g, 16,69 mmol). The reaction was stirred at room temperature for 1 h before diethylether was added and the insoluble salts were filtered. Silica gel was added to the filtrate prior to the solvent removal under vacuum. The dry silica gel was packed, and the adsorbed product was purified by flash chromatography (hexane/EtOAc 10:0 to 7:3) to give 3-(((ieri-butyldimethylsilyl)oxy)methyl)-2-fluoro-4-iodopyridine as a white solid (4.5 g). LC/MS m/z 368 [M+H]+.

The synthetic route of 171366-19-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CONSTELLATION PHARMACEUTICALS, INC.; ALBRECHT, Brian K.; AUDIA, James Edmund; COTE, Alexandre; GEHLING, Victor S.; HARMANGE, Jean-christophe; HEWITT, Michael C.; LEBLANC, Yves; NAVESCHUK, Christopher G.; TAYLOR, Alexander M.; VASWANI, Rishi G.; WO2012/75383; (2012); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 91-02-1, name is Phenyl(pyridin-2-yl)methanone. This compound has unique chemical properties. The synthetic route is as follows. Safety of Phenyl(pyridin-2-yl)methanone

Phenylpyridinone (36.5mg, 0.2mmol), dichlorantin (39.4mg, 0.2mmol) and Pd (OAc) 2 (4.5mg, 0.02mmol),2mL of dichloroethane was added, and the reaction was carried out at 90 C for 12h. Purified by thin-layer chromatography to obtain 21.7mg of 2-chlorophenylpyridylmethanone with a yield of 50.0%.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 91-02-1, Phenyl(pyridin-2-yl)methanone.

Reference:
Patent; China Three Gorges University; Liu Qixing; Chen Yongsheng; Zhang Yin; Chen Danyi; Wen Simiaomiao; Zhao Rongrong; Liu Yiheng; Zhou Haifeng; (14 pag.)CN110563641; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem