Pyridine-derivatives

Electric Literature of 1073182-59-8 , The common heterocyclic compound, 1073182-59-8, name is Methyl 5-amino-2-chloroisonicotinate, molecular formula is C7H7ClN2O2, 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.

[00481] To a stirred solution of (5-amino-2-chloro-isonicotinic acid methyl ester (1.3 g, 7 mmol) in DCM (30 mL) was added Et3N (1.4 g, 14 mmol) and cyclopropanecarbonyl chloride (1.1 g, 10.5 mmol) at 0 C. The mixture was stirred at room temperature overnight. The mixture was evaporated in vacuum. The residue was diluted with water (50 mL). The aqueous phase was extracted with EA (80 mL x2). The extracts were washed with water, dried over anhydrous Na2S04 and filtered. The filtrate was evaporated in vacuum to residue, which was purified by silica gel chromatography (from PE to PE/EA = 10/1) to give (1.0 g, yield: 56 %) of 2-chloro-5-(cyclopropanecarbonyl-amino)-isonicotinic acid methyl ester as yellow solid. ‘H NMR (400MHZ, DMSO-i/6): delta = 10.56 (brs, 1H), 8.79 (s, 1H), 7.23 (s, 1H), 3.82 (s, 3H), 1.87- 1.80 (m, 3H), 0.94-0.83 (m, 4H).

The synthetic route of 1073182-59-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HEDRICK Michael P.; HERSHBERGER Paul M.; MALONEY Patrick R.; PEDDIBHOTLA Satyamaheshwar; PINKERTON Anthony B.; WO2015/200534; A2; (2015);,
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.624-28-2, name is 2,5-Dibromopyridine, molecular formula is C5H3Br2N, molecular weight is 236.892, as common compound, the synthetic route is as follows.Recommanded Product: 2,5-Dibromopyridine

The suspension of 11a (3.12g, 13.11mmol) in 15mL of morpholine was reacted under microwave condition for lOOmin at 12O0C. After the reaction was complete, 20OmL of ethyl acetate was added. The resulting solution was washed with 0.1N HCl (5OmL), water (10OmL), 0.1N NaOH (5OmL) and water (10OmL) subsequently. The resulting organic layer was dried over anhydrous Na2SCK and evaporated to provide lib (3.19g, 99.7%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,624-28-2, 2,5-Dibromopyridine, and friends who are interested can also refer to it.

Reference:
Patent; XCOVERY, INC.; WO2008/88881; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 907545-47-5, name is 2-Chloro-5-nitroisonicotinic acid, molecular formula is C6H3ClN2O4, 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. Formula: C6H3ClN2O4

Synthesis of the compound 34 The compound 33 (3 g, 0.017 mol) was added into thionyl chloride (20 mL), two drops of DMF was added to the above mixture, and then refluxed for 2 h. The thionyl chloride was evaporated off, an acetone (20mL) was added and stirred in an ice bath, ammoniae gas was charged, and then the reaction was run for 1 h before completed. Acetone was evaporated off, 30 mL of water and 30 mL of ethyl acetate were added to the residue, and then extraction was performed. The ethyl acetate layer was washed with the saturated aqueous solution of table salt and evaporated to being dry. The resulted product was recrystallized in ethanol (95percent) to obtain 0.8 g of a white solid product with a yield of 23.5percent. The melting point is 193.4-193.7°C(ethanol).

With the rapid development of chemical substances, we look forward to future research findings about 907545-47-5.

Reference:
Patent; Beijing Yiling Bioengineering Co., Ltd.; EP2366691; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 760207-83-8, name is 3-Bromo-5-chloropicolinonitrile. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 760207-83-8

A microwave vial was charged with 3-bromo-5-chloropicolinonitrile (1.40 g, 6.44 mmol) and dichlorobis(triphenyl-phosphine)palladium (II) (0.54 g, 0.77 mmol). The vial was evacuated and backfilled with nitrogen and 1,4-dioxane (10 mL) was added, followed by tri-n-butyl(vinyl)tin (2.45 mL, 7.73 mmol). The reaction mixture was heated at 100 C. for 1 h. The reaction mixture was diluted with water and EtOAc. The solvent was removed under reduced pressure. The crude material was absorbed onto a plug of silica gel and purified by chromatography through a Redi-Sep pre-packed silica gel column (40 g), eluting with a gradient of 10% to 50% EtOAc in hexane, to provide 5-chloro-3-vinylpicolinonitrile (0.72 g, 4.37 mmol, 67.9% yield) as white solid. [0908] 1H NMR (400 MHz, CHLOROFORM-d) delta 8.54 (d, J=2.25 Hz, 1H), 7.97 (dd, J=0.44, 2.30 Hz, 1H), 7.05 (dd, J=11.20, 17.56 Hz, 1H), 6.05 (d, J=17.41 Hz, 1H), 5.76 (d, J=11.05 Hz, 1H).

With the rapid development of chemical substances, we look forward to future research findings about 760207-83-8.

Reference:
Patent; WHITE, Ryan; ALLEN, Jennifer R.; EPSTEIN, Oleg; HONG, Fang-Tsao; HUA, Zihao; HUMAN, Jason Brooks; LOPEZ, Patricia; OLIVIERI, Philip R.; ROMERO, Karina; SCHENKEL, Laurie; STELLWAGEN, John; TAMAYO, Nuria A.; ZHENG, Xiao Mei; US2014/213581; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 70298-88-3, 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. 70298-88-3, name is 2,2-Dimehtyl-N-pyridin-3-yl-propionamide, molecular formula is C10H14N2O, 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.

nBuLi (2.5M in hexanes, 56.2 ml_, 140.5 mmol) was dropwise added to a solution of the title compound of Preparation 1a (10 g, 56.2 mmol) and N,N,N’,N’-tetramethylethylene- diamine (TMEDA) (20.9 ml_, 140.5 mmol) in diethyl ether (338 ml.) at -78 0C under argon and the resulting mixture was stirred at that temperature for 15 minutes and at -10 0C for 2 hours. Then, the reaction mixture was cooled down to -780C and 2-methoxybenzaldehyde (19.52 g, 140.5 mmol) in 34 ml_ of dry tetrahydrofuran was carefully added. After 15 minutes, the cooling bath was removed and the mixture stirred overnight at room temperature. Subsequently, water (100 mL) was added to the flask and it was extracted with ethyl acetate (3 x 200 mL), the organic solution was washed with brine, dried over sodium sulphate and the solvent removed under reduced pressure. The residue was purified by column chromatography on silica flash, using hexane/ethyl acetate (4:1 ) as eluents, to yield the title compound (11.1 g, 63%) as a solid.

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 70298-88-3, 2,2-Dimehtyl-N-pyridin-3-yl-propionamide.

Reference:
Patent; LABORATORIOS ALMIRALL, S.A.; WO2007/96072; (2007); 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. 55338-73-3, name is 5-Amino-2-pyridinecarbonitrile. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C6H5N3

A 18 ml vial was loaded with a mixture of 30% H2O2 (1 ml), 3N NaOH (3 ml) and MeOH (2.5 ml). To this mixture 5-Amino-pyridine-2-carbonitrile (450 mg, 3.78 mmole) was added at room temperature. Reaction mixture was stirred at rt for 45 minutes, TLC showed the starting material to be consumed. The mixture was diluted with water and filtered; the solid was washed with water and dried to give 480 mg product, 92% yield.

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, 55338-73-3, 5-Amino-2-pyridinecarbonitrile.

Reference:
Patent; Nivalis Therapeutics, Inc.; Wasley, Jan; Rosenthal, Gary J.; Sun, Xicheng; Strong, Sarah; Qiu, Jian; US9138427; (2015); B2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 588729-99-1, 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 588729-99-1, name is 3-Amino-5-bromo-2-chloropyridine. This compound has unique chemical properties. The synthetic route is as follows.

Thionyl chloride (60.1 mL, 823 mmol) was added dropwise over 60 min to water (361 mL), cooled to 0 C, maintaining the temperature of the mixture 0-7 C. The solution was allowed to warm to 18 C over 17 h. copper(l) chloride (218 mg, 2.2 mmol) was added to the mixture, and the resultant yellow-green solution was cooled to -3 C using an acetone/ ice bath. 2) HCI (195 mL, 6.418 mol)(37% w/w) was added, with agitation, to 5-bromo-2-chloro-3- pyridineamine (25 g, 121 mmol), maintaining the temperature of the mixture below 30 C with ice cooling. The reaction mixture was cooled to -5 C using an ice/acetone bath and a solution of sodium nitrite (14.72 g, 213 mmol) in water (58 mL) was added dropwise over 45 min, maintaining the temperature of the reaction mixture between -5 to 0 C, the resultant slurry was cooled to -2 C and stirred for 10 min.3) The slurry from step (2) was cooled to -5 C and added to the solution obtained from step 1 ) over 30 min, maintaining the temperature of the reaction mixture between -3 to 0 C ( the slurry from step b was maintained at -5 C throughout the addition). As the reaction proceeded, a solid began to precipitate. When the addition was complete, the reaction mixture was agitated at 0 C for 75 min. The suspended solid was collected by vacuum filtration, washed with water, and dried under vacuum to give 5- bromo-2-chloro- 3-pyridinesulfonyl chloride. ES-LCMS: m/z 271 .94, 269.97 (M-1 ).

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 588729-99-1, 3-Amino-5-bromo-2-chloropyridine.

Reference:
Patent; GLAXOSMITHKLINE LLC; BANKA, Anna, Lindsey; BOTYANSZKI, Janos; DICKERSON, Scott, Howard; DUAN, Maosheng; LEIVERS, Martin, Robert; MCFADYEN, Robert, Blount; MOORE, Christopher, Brooks; REDMAN, Aniko, Maria; SHOTWELL, John, Bradford; TAI, Vincent, W.-F.; TALLANT, Matthew, David; XUE, Jianjun; WO2012/37108; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 131747-61-0, (2-(Trifluoromethyl)pyridin-4-yl)methanol, 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, 131747-61-0, blongs to pyridine-derivatives compound. Recommanded Product: (2-(Trifluoromethyl)pyridin-4-yl)methanol

534 tert-Butyl N-[(3-hydroxyphenyl)methyl]carbamate (0.18 g, 1.0 mmol), E-1 (0.22 g, 1.0 mmol) and 13 triphenylphosphine (0.39 g, 1.5 mmol) were dissolved in 12 dichloromethane (3 mL), 236diisopropyl azodicarboxylate (0.32 mL, 1.5 mmol) was added, and the mixture was stirred at roomtemperature for 1 hr. The reaction mixture was concentrated under reduced pressure and the obtained residuewas purified by silica gel column chromatography (hexane/ethyl acetate). To the obtained compound wasadded 4 mol/L 114 hydrochloric acid (1,4-dioxane solution, 3 mL), and the mixture was stirred at roomtemperature for 1 hr, and concentrated under reduced pressure to give the 535 title compound ( 0.13 g ,0.40 mmol, 40%) MS (ESI) m/z 283 (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,131747-61-0, its application will become more common.

Reference:
Patent; EA PHARMA CO., LTD.; KOBAYASHI, Kaori; SUZUKI, Tamotsu; KAWAHIRA, Mizuki; FUJII, Tomohiro; SUGIKI, Masayuki; OHSUMI, Koji; OKUZUMI, Tatsuya; (285 pag.)US2016/332999; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 67625-37-0, 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 67625-37-0, name is Ethyl 6-bromoimidazo[1,2-a]pyridine-2-carboxylate. This compound has unique chemical properties. The synthetic route is as follows.

Preparation 86 6-Aminoimidazo[1,2-a]pyridine-2-carboxamide To a solution of ethyl 6-aminoimidazo[1,2-a]pyridine-2-carboxylate (Preparation 87, 2 g, 0.0074 mol) in MeOH (30 mL) was added ammonia (3 g, 0.044 mol) and the reaction was heated to 100 C. in a sealed vessel for 24 hours. The reaction was cooled and concentrated in vacuo to afford the title compound (1.9 g, 90%).

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 67625-37-0, Ethyl 6-bromoimidazo[1,2-a]pyridine-2-carboxylate.

Reference:
Patent; PFIZER INC.; Fensome, Andrew; Gopalsamy, Ariamala; Gerstenberger, Brian S.; Efremov, Ivan Viktorovich; Wan, Zhao-Kui; Pierce, Betsy; Telliez, Jean-Baptiste; Trujillo, John I.; Zhang, Liying; Xing, Li; (104 pag.)US2016/52930; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1210419-26-3, Adding some certain compound to certain chemical reactions, such as: 1210419-26-3, name is Methyl 6-bromo-5-fluoropicolinate,molecular formula is C7H5BrFNO2, 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 1210419-26-3.

Synthesis of methyl 6-(2,6-difluoro-4-(4-hvdroxytetrahvdro-2H-pyran-4-yl)phenyl)-5- fluoropicolinate Method 1 was followed using methyl 6-bromo-5-fluoropicolinate (1.0 equiv.) and 4-(3,5-difluoro-4-(4,4,5,5-tetramethyl-l ,3,2-dioxaborolan-2-yl)phenyl)tetrahydro-2H- pyran-4-ol (1.8 equiv.) at 100 C for 20 min in microwave to give methyl 6-(2,6-difluoro- 4-(4-hydroxytetrahydro-2H-pyran-4-yl)phenyl)-5-fluoropicolinate. LC/MS = 368.0 (MH+), R, = 0.75 min.

According to the analysis of related databases, 1210419-26-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; BURGER, Matthew; NISHIGUCHI, Gisele; RICO, Alice; SIMMONS, Robert Lowell; TAMEZ, JR., Victoriano; TANNER, Huw; WAN, Lifeng; WO2014/33631; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem