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. 1427-06-1, name is Methyl 6-fluoropyridine-3-carboxylate, the common compound, a new synthetic route is introduced below. HPLC of Formula: C7H6FNO2

(a) (2S,5R)-4-(5-Methoxycarbonyl-pyridin-2-yl)-2,5-dimethyl-piperazine-1-carboxylic acid tert-butyl ester A mixture of 6-fluoronicotinic acid methyl ester (1.0 g, 6.4 mmol), (2S,5R)-2,5-dimethyl-piperazine-1-carboxylic acid tert-butyl ester HCl (1.6 g, 6.4 mmol), and potassium carbonate (1.78 g, 12.9 mmol) were stirred in DMSO (10 mL) at 120 C. for 2 h, cooled, diluted with ethyl acetate (50 mL), washed with water (2*10 mL), dried over magnesium sulfate, filtered and concentrated.

The synthetic route of 1427-06-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THERAVANCE, INC.; US2012/114600; (2012); A1;,
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

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

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

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

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

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

Adding a certain compound to certain chemical reactions, such as: 62733-99-7, Methyl 3-hydroxypicolinate, 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, 62733-99-7, blongs to pyridine-derivatives compound. SDS of cas: 62733-99-7

To a solution of 3-hydroxy-pyridine-2-carboxylic acid methyl ester (200 mg, 1.3 mmol) in N,N-dimethylformamide (2.0 ml) was added at 22 0C sodium hydride (55% in oil, 64 mg) and stirring was continued until gas evolution ceased. The suspension was cooled to 0 0C and treated with trifiuoro ethyl trifiuormethanesulfonate (728 mg) and stirring was continued at 22 0C for 2 hours. The mixture was partitioned between saturated sodium hydrogen-carbonate solution and ethyl acetate, and the organic layer was dried and evaporated. The residue was purified by chromatography on silica using n-heptane and ethyl acetate (3:1) as the eluent to give 3-(2,2,2- trifluoro-ethoxy)-pyridme-2-carboxylic acid methyl ester as a pale green oil. Mass (calculated) C9H8F3NO3 [235.16]; (found) [M+H]+ = 236

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,62733-99-7, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; SIENA BIOTECH S.P.A; ANDREINI, Matteo; BANNER, David; GUBA, Wolfgang; HILPERT, Hans; MAUSER, Harald; MAYWEG, Alexander, V.; NARQUIZIAN, Robert; POWER, Eoin; ROGERS-EVANS, Mark; TRAVAGLI, Massimiliano; VALACCHI, Michela; WOLTERING, Thomas; WOSTL, Wolfgang; WO2011/20806; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 588729-99-1, Adding some certain compound to certain chemical reactions, such as: 588729-99-1, name is 3-Amino-5-bromo-2-chloropyridine,molecular formula is C5H4BrClN2, 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 588729-99-1.

N-(5-Bromo-2-chloro-3-pyridinyl)methanesulfonamide 5-Bromo-2-chloro-3-pyridinamine [commercially available] (10 g, 48.2 mmol) was dissolved in pyridine (75 ml) and methanesulfonyl chloride (7.46 ml, 96 mmol) added, and the mixture stirred overnight. Further methanesulfonyl chloride (2.1 ml) was added and the reaction stirred at room temperature for 5 h. A further portion of methanesulfonyl chloride (2.1 ml) was added and the mixture stirred at room temperature overnight. The pH was adjusted to ?pH6 by the addition of 2M hydrochloric acid. The mixture was then extracted with dichloromethane (2*150 ml) the combined organic layers were dried using a hydrophobic frit and the solvent removed in vacuo. The residue was suspended in methanol (200 ml) and 2M sodium hydroxide (50 ml) added. The mixture was stirred for 1 h and then the solvent removed in vacuo. The residue was dissolved in water (250 ml) and extracted with dichloromethane (150 ml). The aqueous layer was then acidified and the resulting precipitate collected by filtration. The solid was air dried overnight to give the title compound as an off white solid (13.45 g).

According to the analysis of related databases, 588729-99-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Glaxo Group Limited; Hamblin, Julie Nicole; Jones, Paul Spencer; Keeling, Suzanne Elaine; Le, Joelle; Mitchell, Charlotte Jane; Parr, Nigel James; (136 pag.)US9326987; (2016); B2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 14482-51-0, 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.14482-51-0, name is 2-Bromo-3,5-dichloropyridine, molecular formula is C5H2BrCl2N, molecular weight is 226.89, as common compound, the synthetic route is as follows.

A mixture of 2-bromo-3,5-dichloropyridine (5.672 g, 25 mmol), sodium iodide (11241.7 mg, 75 mmol) and chlorotrimethylsilane (2716 mg, 25 mmol) in MeCN (50 mL) was heated under reflux for 45 min. The reaction mixture was then poured into a 2.0 M aqueous solution of sodium hydroxide (10 mL) and extracted with diethyl ether (20 mL x 3). The combined organic layers were washed with brine and evaporated to afford crude product, which was purified by biotage (EtOAc/PE=l% ~ 10%, ISCO 40 g, 25 mL/min, normal phase silica gel, uv 254) to afford the target compound 3,5- dichloro-2-iodopyridine (3800 mg, 55.5 % yield) as a white solid. 1H NMR (400 MHz, MeOD) delta 8.35 (t, J= 4.5 Hz, 1H), 8.01 (d, J= 2.3 Hz, 1H). GC-MS m/z calcd for [C5H2C12IN]: 272.9; found: 273.0.

Statistics shows that 14482-51-0 is playing an increasingly important role. we look forward to future research findings about 2-Bromo-3,5-dichloropyridine.

Reference:
Patent; GALECTO BIOTECH AB; BRIMERT, Thomas; JOHNSSON, Richard; LEFFLER, Hakon; NILSSON, Ulf; ZETTERBERG, Fredrik; (284 pag.)WO2016/120403; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem