Pyridine-derivatives

Synthetic Route of 849937-96-8, 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.849937-96-8, name is 5-Bromo-2,4-dichloropyridine, molecular formula is C5H2BrCl2N, molecular weight is 226.8861, as common compound, the synthetic route is as follows.

To a stirred solution of 5-bromo-2,4-dichloropyridine (3.0 g, 13.22 mmol),isopropylamine (1.7 mL, 19.83 mmol), and Hunig?s Base (11.6 mL, 66.1 mmol) in DMF(5 mL) at room temperature was then heated at 120 C behind a safety shield for 4 hours,at which point it was judged to be complete by LCMS. The reaction mixture was diluted with ethyl acetate and washed 10% LiC1 (3x). The organic layer was dried over Na2SO4, filtered and concentrated to afford the crude product. The product was purified by column chromatography (hexanes/EtOAc) to afford 5 -bromo-2-chloro-N-isopropylpyridin-4-amine (1.29 g, 37% yield) as a colorless oil. LCMS m/z 249.0 (M+H).

Statistics shows that 849937-96-8 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-2,4-dichloropyridine.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; DUNCIA, John V.; GARDNER, Daniel S.; HYNES, John; MACOR, John E.; SANTELLA, Joseph B.; WU, Hong; NAIR, Satheesh Kesavan; PAIDI, Venkatram Reddy; SARKUNAM, Kandhasamy; SISTLA, Ramesh Kumar; POLIMERA, Subba Rao; (72 pag.)WO2016/210037; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 800401-67-6, Adding some certain compound to certain chemical reactions, such as: 800401-67-6, name is Ethyl 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylate,molecular formula is C10H9ClN2O2, 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 800401-67-6.

Step 3: synthesis of ethyl 5-chloro-l-(4-fluorobutyl)-lH-pyrrolo[2,3-c]pyridine-2- carboxylate 10-cTo a solution of ethyl 5-chloro-lH-pyrrolo[2,3-c]pyridine-2-carboxylate 10-b (1.9 g, 8.458 mmoles) in acetonitrile (85 mL) was added cesium carbonate (3.306 g, 1.2 eq). This mixture was stirred at room temperature for one hour and then l-bromo-4- fluorobutane (1.089 g, 1.2 eq) was added and stirring at 60C continued overnight. The reaction mixture was filtered over a glass filter and the filtrate was evaporated to dryness. The residue was taken up in dichloromethane and washed with water twice. The organic layer was dried over MgS04, filtered and evaporated. The residue was recrystallised from diisopropylether. The crystals were collected by filtration and dried in vacuo to give 2.19 g (87% yield) of the targeted compound 10-c. m/z = 299 (M+H)+.

According to the analysis of related databases, 800401-67-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN R&D IRELAND; COOYMANS, Ludwig Paul; DEMIN, Samuel Dominique; HU, Lili; JONCKERS, Tim Hugo Maria; RABOISSON, Pierre Jean-Marie Bernard; TAHRI, Abdellah; VENDEVILLE, Sandrine Marie Helene; WO2012/80450; (2012); A1;,
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.114077-82-6, name is 4-Chloronicotinaldehyde, molecular formula is C6H4ClNO, molecular weight is 141.56, as common compound, the synthetic route is as follows.Product Details of 114077-82-6

Step 2: The mixture of 4-chloronicotinaldehyde 2 (4.6 g, 32.6 mmol), 2- methyl-2-propanethiol (4.4 mL, 32.6 mmol), K2CO3 (9.0 g, 65.2 mmol) and DMF (70 mL) was stirred at 100C for 12 h until TLC indicate no 4-chloronicotinaldehyde was existed. The reaction mixture was diluted with water, extracted with EA and the organic layer was concentrated. The residue was purified by column chromatography (P.E/EA 12: 1) to afford 6.3 g clear oil, yield 99%. 1HNMR (400 MHz, CDCl3): 10.63 (s, 1H), 9.03 (s, 1H), 8.65 (d, 1H), 7.50 (d, 1H), 1.40 (s, 9H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,114077-82-6, 4-Chloronicotinaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; ACHAOGEN, INC.; WO2009/55696; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 88912-27-0, 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.88912-27-0, name is 3-Chloroisonicotinic acid, molecular formula is C6H4ClNO2, molecular weight is 157.55, as common compound, the synthetic route is as follows.

A mixture of 0.69 g of 3-chloroisonicotinic acid, 5 ml of thionyl chloride and 30 mg of DMF was heated to reflux for 3.5 hours. The reaction mixture was cooled to room temperature, and then the reaction mixture was concentrated under reduced pressure to give 3-chloroisonicotinic acid chloride. A mixture of the resultant 3-chloroisonicotinic acid chloride and 4 ml of DMF was added dropwise to a mixture of 0.85 g of 2-amino-5-fluoro-4- trifluoromethylphenol, 0.88 g of triethylamine and 4 ml of DMF while ice-cooling.Thereafter, the reaction mixture was stirred at room temperature for one hour and at 50C for one hour. The reaction mixture was cooled to room temperature, and then water was added, followed by extraction with ethyl acetate twice. The combined organic layers wee washed with water and a saturated sodium chloride solution, then dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resultant solid was washed with diethyl ether to give 0.77 g of 3-chloro-N-[4-fluoro-2-hydroxy-5-(trifluoromethyl)phenyl]- isonicotinamide.-NMR (DMSO-d6) delta: 10.20 (br s, 1H), 8.75 (s, 1H), 8.64 (d, J=4.8 Hz, 1H), 8.23 (d, J=8.5 Hz, 1H), 7.62 (d, J=4.8 Hz, 1H), 6.91-6.85 (m, 1H)

Statistics shows that 88912-27-0 is playing an increasingly important role. we look forward to future research findings about 3-Chloroisonicotinic acid.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; OTSUKI, Junko; WO2011/49220; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 849067-90-9, 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 849067-90-9 as follows.

3-Iodo-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde A solution of 1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde (Intermediate 3a) (2.4 g, 16.3 mmol, 1.0 eq.) and NIS (3.7 g, 16.3 mmol, 1.0 eq.) in DMF (25 mL) was stirred at rt overnight. The reaction mixture was diluted with water (50 mL) and a saturated solution of Na2SO3 (2 mL). The formed precipitate was collected by filtration, rinsed with water and dried to give 3-iodo-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde (Intermediate 3b) as a solid (4.0 g; yield: 91percent; UPLC purity: 100percent).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,849067-90-9, its application will become more common.

Reference:
Patent; Felicitex Therapeutics, Inc.; Selvita S.A.; Dreas, Agnieszka; Fabritius, Charles-Henry; Dzienia, Andrzej; Buda, Anna; Galezowski, Michal; Kachkovskyi, Georgiy; Kulesza, Urszula; Kucwaj-Brysz, Katarzyna; Szamborska-Gbur, Agnieszka; Czardybon, Wojciech; Vilenchik, Maria; Frid, Michael; Kuznetsova, Alexandra; (98 pag.)US2018/179199; (2018); 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. 55934-00-4, name is 3,4-Dichloropyridine, the common compound, a new synthetic route is introduced below. SDS of cas: 55934-00-4

To a solution of 2,2,6,6-tetramethylpiperidine (1.56 g, 11 mmol) in dry ether (20 mL) at 0 C was added n-BuLi (4.4 mL, 2.5 M in THF, 11 mmol) slowly. The reaction mixture was stirred at this temperature for 30 min before cooled to -78 C. A solution of 3,4-dichloropyridine (1.48 g, 10 mmol) in dry ether (5 mL) was injected via syringe to the above reaction mixture and stirred for 2 h before trimethylsilyl isothiocyanate (15 mmol) was added. After warmed to room temperature, the reaction was quenched by the addition of HOAc (2 mL) and water (10 mL), and then let to stir overnight. The suspension was filtered and washed with cold water, giving the title compound as a gray solid (686 mg, 40%). 1H-NMR (DMSO-d6, 600 MHz) delta 8.50 (d, 1H,J = 5.2 Hz, ArH), 8.12 (br s, 1H, CONH2), 7.83 (d, 1H, J = 5.2 Hz, ArH), 7.82 (br s, 1H, CONH2).

The synthetic route of 55934-00-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Wei; Ai, Jing; Shi, Dakuo; Peng, Xia; Ji, Yinchun; Liu, Jian; Geng, Meiyu; Li, Yingxia; Molecules; vol. 19; 2; (2014); p. 2655 – 2673;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 524955-09-7, 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 524955-09-7, name is 3-Chloro-4-(pyridin-2-ylmethoxy)aniline. This compound has unique chemical properties. The synthetic route is as follows.

0.500 g (2.14 mmol) of 3-chloro-4-(pyridin-2-ylmethoxy)aniline, 0.317 g (2.14 mmol) of 2,4-dichloropyrimidine, 0.499 g (4.28 mmol)Triethylamine and 5 mL of ethanol were added to the reaction flask and refluxed at 79 C for 6 h.After the reaction, it was cooled to room temperature. The solvent was removed by steaming under reduced pressure.Add 10mL of water,Extract with ethyl acetate (3 x 15 mL) and combine the organic phases.The organic phase is dried over anhydrous sodium sulfate and concentrated.Separated by silica gel column chromatography (dichloromethane: ethyl acetate = 1:20, V/V).Obtained as a pale yellow solid 2-(3-chloro-4-(pyridin-2-ylmethoxy)phenylamino)-4-chloropyrimidine0.496 g, the yield is 67%.

According to the analysis of related databases, 524955-09-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shaanxi Normal University; Li Baolin; Hao Yunxia; Zhang Yaling; Li Xiabing; Wang Wei; (22 pag.)CN109516959; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 932-35-4 ,Some common heterocyclic compound, 932-35-4, molecular formula is C6H4N2O, 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.

(1) 2-Cyano-3-hydroxypyridine (3.00 g) is dissolved in acetonitrile/water (5:1, 90 ml), and N-bromosuccinic imide (5.34 g) is added thereto in small portions under ice-cooling. The mixture is then stirred for 2 hours under the same cooling conditions. The reaction solution is diluted with ethyl acetate, washed with water and saturated brine successively and dried over sodium sulfate. The solvent is removed by evaporation under reduced pressure to give crude 6-bromo-3-hydroxypyridine-2-carbonitrile (6.26 g). ESI-MS M/Z:197/ 199[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,932-35-4, its application will become more common.

Reference:
Patent; TANABE SEIYAKU CO., LTD.; EP1582521; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 178876-82-9, 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. 178876-82-9, name is Methyl 6-amino-5-bromopicolinate. A new synthetic method of this compound is introduced below.

c. 6-Amino-5-bromopyridine-2-carboxylic acid methyl ester (2 g) and a 50% aqueous solution of chloroacetaldehyde (2.8 mL) in isopropanol (100 mL) were stirred heated to 70C overnight. More of the 50%> aqueous solution of chloroacetaldehyde (0.35 mL) was added at room temperature and the mixture was stirred heated to 80C for an additional 3 hours. The mixture was cooled to room temperature, loaded on silica and purified by chromatography (Si02, Heptane/EA) to afford afford 8-bromo-imidazo[l,2-a]pyridine-5-carboxylic acid methyl ester as a solid (2.3 g). MS (ES): M/Z [M+H]=255. IH NMR (400 MHz, CHLOROFORM-d): 4.00 (s, 3H), 7.51 (d, J=7.6 Hz, IH), 7.63 (d, J=7.8 Hz, IH), 7.82 (s, IH) and 8.90 (s, IH)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,178876-82-9, Methyl 6-amino-5-bromopicolinate, and friends who are interested can also refer to it.

Reference:
Patent; MERIAL LIMITED; LE HIR DE FALOIS, Loic, Patrick; LEE, Hyoung, Lk; WILKINSON, Douglas, Edward; BECK, Brent, Christopher; WO2011/75591; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 183208-35-7, 5-Bromo-1H-pyrrolo[2,3-b]pyridine, 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, 183208-35-7, blongs to pyridine-derivatives compound. category: pyridine-derivatives

A mixture of 5-Bromo-1H-pyrrolo[2,3-b]pyridine (50 g, 252.5 mmol) and N-iodosuccinimide (13.6 g, 60.6 mmol) in dichloroethane (200 ml) was stirred at 95 C. overnight. The reaction was allowed to cool to room temperature and saturated Na2H2SO4 (200 ml) was added. The mixture was then extracted with ethyl acetate (400 ml×2). The combined organic layers were dried with Na2SO4, concentrated. Silica gel chromatography of the crude using a gradient of ethyl acetate and hexane afforded 5-bromo-3-iodo-1H-pyrrolo[2,3-b]pyridine (62.8 g, 77% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,183208-35-7, its application will become more common.

Reference:
Patent; SGX Pharmaceuticals, Inc.; US2008/261921; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem