Category: pyridine-derivatives

Reference of 3430-18-0, Adding some certain compound to certain chemical reactions, such as: 3430-18-0, name is 2,5-Dibromo-3-methylpyridine,molecular formula is C6H5Br2N, 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 3430-18-0.

[0231] A solutionof2,5-dibromo-3-methylpyridine (1) 3 g,12.1 mmol) in methanol (20 ml) was added sodium methoxide(2M, 20 mL) and refluxed at 100 C. for 2 h. The reactionmixture was poured on ice water and neutralized with aqueoushydrochloric acid (1M) and extracted with dichloromethane(2×15 ml). The combined organic layer waswashed with water, brine, dried over sodium sulfate, andconcentrated at reduced pressure to give 5-Bromo-2-methoxy-3-methyl-pyridine (35), which was used without furtherpurification (1.9 g, 77.8%).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 3430-18-0, 2,5-Dibromo-3-methylpyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Naik, Maruti N.; PEER MOHAMED, Shahul Hameed; Shandil, Radha K.; Shinde, Vikas Narayan; Shirude, Pravin S.; Chatterji, Monalisa; US2015/25087; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 92992-85-3, Adding some certain compound to certain chemical reactions, such as: 92992-85-3, name is 2-Bromo-3,5-dimethylpyridine,molecular formula is C7H8BrN, 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 92992-85-3.

To a mixture of 2-methylpiperazine-1-carboxylic acid tert-butyl ester (2 g),2-bromo-3,5-dimethylpyridine (1.95 g),tris(dibenzylideneacetone)dipalladium(0)(183 mg),rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (250 mg) and tert-butoxy sodium (1.3 g) was added toluene (33 mL) and the mixture was stirred with heating under reflux for 8 hr. The reaction mixture was cooled and filtered through celite. The filtrate was evaporated and the obtained residue was purified by column chromatography (hexane:ethyl acetate)to give 4-(3,5-dimethylpyridin-2-yl)-2-methylpiperazine-1-carboxylic acid tert-butyl ester (1.61 g). MS(ESI)m/z:206(M+H)+

According to the analysis of related databases, 92992-85-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Mitsubishi Tanabe Pharma Corporation; ISHIBUCHI, Seigo; SARUTA, Kunio; HAMADA, Maiko; MATOBA, Nobuatsu; MATSUDAIRA, Tetsuji; SEKI, Maki; TARAO, Akiko; HONJO, Takashi; OGATA, Shingo; KAWATA, Atsushi; MOROKUMA, Kenji; FUJIE, Naoto; AOYAMA, Yukio; (251 pag.)EP3321256; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 850663-54-6, 4-Chloro-5-nitropyridin-2(1H)-one, 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, SDS of cas: 850663-54-6, blongs to pyridine-derivatives compound. SDS of cas: 850663-54-6

A mixture of 4-chloro-2-hydroxy-5-nitropyridine (3.00 g, 17.2 mmol), phenylboronic acid (2.51 g, 20.6 mmol), PdC12(dppf)-CH2Cl2adduct (1.40 g, 1.72 mmol), and potassium carbonate (4.75 g, 34.4 mmol) in THF (100 mL) was heated at 85 C for 16 h. The product mixture was cooled and partitioned between water and ethyl acetate (3x). The combined organic layers were dried over Na2504, filtered and concentrated. The residue was purified by flash column chromatography (5i02 cartridge), eluting withMeOH/CH2C12 (0-10%) to afford the title compound. MS: m/z = 217 (M + 1).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,850663-54-6, 4-Chloro-5-nitropyridin-2(1H)-one, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; STUMP, Craig A.; CHEN, Yi Heng; LIU, Ping; MENG, Dongfang; WU, Jane; LI, Chun Sing; QI, Zhiqi; (163 pag.)WO2016/161572; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 405224-23-9, 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. 405224-23-9, name is 5-Bromo-2-chloronicotinonitrile. A new synthetic method of this compound is introduced below.

To a solution of 5-bromo-2-chloronicotinonitrile (1.0 equiv.) in THF and water (4:1, 0.2M) was added potassium carbonate (3.0 equiv.) and 4-methyl-3-(4,4,5,5-tetramethyl- 1,3,2-dioxaborolan-2-yl)aniline (1.0 equiv.) and the solution was degassed with Argon. PdCl2(dppf)-DCM (0.1 equiv.) was added and the solution was refluxed at 90 C for 24 hours. Upon cooling to room temperature, the reaction was partitioned between 1:1 EtOAc/n- heptanes and H2O, mixed, separated, washed with NaCl (sat.) , dried over MgSO4, filtered, concentrated and purified by ISCO SiO2 chromatography (0-80% EtOAc/n-heptanes) to yield 5-(5-amino-2-methylphenyl)-2-chloronicotinonitrile in 82% yield. LCMS (m/z) (M+H) = 243.9, Rt = 0.56 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,405224-23-9, its application will become more common.

Reference:
Patent; NOVARTIS AG; BARSANTI, Paul Andrew; BURGER, Matthew T.; LOU, Yan; NISHIGUCHI, Gisele A.; POLYAKOV, Valery Rostislavovich; RAMURTHY, Savithri; SUBRAMANIAN, Sharadha; TAFT, Benjamin R.; TANNER, Huw Rowland; WAN, Lifeng; (180 pag.)WO2016/38583; (2016); 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. 436799-32-5, name is 5-Bromo-2-(trifluoromethyl)pyridine, the common compound, a new synthetic route is introduced below. Computed Properties of C6H3BrF3N

In a dried 250 mL 3-neck round bottom flask fitted with a stirrer bar, thermometer, and flushed with nitrogen, was placed anhydrous THF (16 mL, Aldrich, inhibitor free) followed by N, N-diisopropylamine (0.895 g, 8.85 mmol, Aldrich, redistilled 99.95% pure). After cooling the stirred solution to -70 0C, n-butyl lithium (3.54 mL of a 2.5M solution in hexanes, 8.85 mmol) was added dropwise, keeping the reaction temperature less than -60 0C. The resulting solution was stirred at -70 0C for a further 10 min, then warmed to -20 0C, before immediately cooling to -90 0C. A solution of 5-bromo-2-(trifluoromethyl)pyridine (2 g, 8.85 mmol) in anhydrous THF (8 ml_, Aldrich, inhibitor free) was added dropwise, keeping the reaction temperature less than -85 0C. The resulting orange solution was stirred at -90 0C for 40 min.In a separate dried 250 ml_ 3-neck round bottom flask fitted with a stirrer bar, thermometer, and flushed with nitrogen, was placed anhydrous THF (5 ml_, Aldrich, inhibitor free) followed by methyl iodide (5 ml_, 80 mmol). The solution was cooled to -90 0C. To this was added (via cannula) the solution of the pre-formed lithiated pyridine, controlling the rate so as to keep the reaction temperature of the receiving flask less than -80 0C. The resulting dark solution was stirred at -90 0C for a further 15 min (LCMS indicated reaction complete). The reaction was quenched with sat aq. NH4CI solution (50 mL), then allowed to slowly warm to rt. Organics were extracted with EtOAc (2 x 50 mL), then the combined organic layers washed with water (50 mL), then brine (50 mL), separated, dried over MgSO4, and then filtered. Concentration in vacuo gave 1.68 g of a brown oil which was purified via short-path vacuum distillation (45-46 0C, ca. 5 mmHg) to give 5-bromo-4-methyl-2- (trifluoromethyl)pyridine 1-2 (0.289 g, 14%) as a yellow oil (>97% pure). MS (M + H)+: 241.8, tR = 2.458 min (method 1); 1H NMR (CDCI3) delta 8.74 (1H, s), 7.56 (1H, s), 2.50 (3H, s).

The synthetic route of 436799-32-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NEUROCRINE BIOSCIENCES, INC.; WO2008/124614; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 880870-13-3 , The common heterocyclic compound, 880870-13-3, name is 5-Bromo-2-chloro-4-methoxypyridine, molecular formula is C6H5BrClNO, 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.

A solution of 5-bromo-2-chloro-4-methoxypyridine (5.0 g, 22.48 mmol) in DMF (80 mL) was purged nitrogen for 15 min. Next, Zn(CN)2 (3.96 g, 33.7 mmol) and Pd(Ph3P)4 (2.60 g, 2.25 mmol) were added, successively. The resulting suspension was stirred at 95C for 12 h under nitrogen atmosphere. The reaction mixture was cooled to ambient temperature and filtered to remove inorganic solid. The solvent (DMF) was evaporated to provide the crude residue as an oil, which was purified on silica gel and eluted with 0 – 30% ethyl acetate/hexanes to afford the product. 1HNMR (500 MHz, DMSO- 6) delta 8.69 (s, 1H), 7.50 (s, 1H), 4.04 (s, 3H); LC/MS: [(M+l)]+ = 169.

The synthetic route of 880870-13-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; PASTERNAK, Alexander; PIO, Barbara; CHOBANIAN, Harry, R.; SHI, Zhi-Cai; DONG, Shuzhi; GUO, Yan; WALSH, Shawn, P.; GUO, Zhiqiang; FERGUSON, Ronald, D.; CATO, Brian; (114 pag.)WO2016/60941; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 106961-33-5, N,N-Dimethyl-1-(6-methyl-2-(p-tolyl)imidazo[1,2-a]pyridin-3-yl)methanamine, 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, name: N,N-Dimethyl-1-(6-methyl-2-(p-tolyl)imidazo[1,2-a]pyridin-3-yl)methanamine, blongs to pyridine-derivatives compound. name: N,N-Dimethyl-1-(6-methyl-2-(p-tolyl)imidazo[1,2-a]pyridin-3-yl)methanamine

80 liters of acetone and 8 kg of 2-(4-methyl phenyl)-3-dimethyl amino methyl-6-methyl-[1,2-alpha] imidazo pyridine were taken into a reactor and the mixture was heated to 39 C. The reaction mixture was maintained at 38 to 39 C. for 20 minutes. The reaction mass was then cooled to 26 C. Methyl iodide was pre-cooled to 15 C. and added to the reaction mass under stirring. The reaction mixture was maintained at 27 to 28 C. for 10 hours. Reaction completion was checked using thin layer chromatography. After the reaction was complete, the reaction mass was filtered and the solid was washed with 8 liters of chilled acetone. Into another reactor 60 liters of water and 1.4 kg of sodium cyanide were added. The wet solid obtained above was also added to the reactor and the reaction mass was heated to 84 C. The reaction mixture was maintained at 82 to 84 C. for 12 hours. Reaction completion was checked using high performance liquid chromatography. After the reaction was completed, the reaction mixture was cooled to 55 C. A solution of 12 liters of 48% aqueous sodium hydroxide solution in 40 liters of water was added to the reaction mass. The reaction mixture was heated to 85 C., and maintained for 3 hours. The temperature was slowly raised to 98 C. and maintained under reflux for 13 hours, 30 minutes. Reaction completion was checked using high performance liquid chromatography. After the reaction was complete, the reaction mixture was cooled to 33 C. and filtered through a Celite bed and the bed was washed with 8 liters of water. The filtrate was taken into a fresh reactor and washed with 40 liters of toluene in two equal lots. The pH of the filtrate was adjusted to 5.3 with 14 liters of acetic acid. After completion of the pH adjustment, the filtrate was maintained at 25 C. for 4 hours. The separated solid was filtered and washed with 16 liters of water in two equal lots. The wet solid was dried at 85 C. and a vacuum of 650 mm Hg for 12 hours to yield 5.6 kg of the title compound. (Yield 69.73%) Purity by HPLC: 98.2%.

The synthetic route of 106961-33-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Padi, Pratap Reddy; Bollikonda, Satyanarayana; Jasty, Ananda Mohan; Tamma, Ranga Reddy; Mohanarangam, Saravanan; Yasareni, Sumalatha; Rupakala, Gowri Shanker; Debasish, Ghosh; US2007/27180; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 887266-57-1, 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.887266-57-1, name is 3-Fluoro-2-hydrazinylpyridine, molecular formula is C5H6FN3, molecular weight is 127.1196, as common compound, the synthetic route is as follows.

This compound is prepared essentially as described in Chem. Ber. (1985) 118:741-752 andFarmaco (1990) 45: 167-186. A mixture of 3,5-diethoxy-penta-2,4-dienoic acid ethyl ester (2.4 g, 11.2 mmol) and (3-fluoro-pyridin-2-yl)hydrazine (1.4 g, 11.0 mmol) in EtOH (30 niL) and concentrated HCl (6 mL) is heated at 900C for 2 hours. The solvent is removed, and the residue is neutralized with saturated NaHCO3 and extracted with DCM. The solution is dried and evaporated, and the residue is column purified (EtOAc:hexane=2: l) to give 103. 1H NMR delta (CDCl3) 1.13 (t, 3H), 3.97 (s, 2H), 4.04 (q, 2H), 6.42 (s, IH), 7.30-7.38 (m, IH), 7.64 (td, IH), 7.72 (s, IH), 8.28 (d, IH).

The chemical industry reduces the impact on the environment during synthesis 887266-57-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; NEUROGEN CORPORATION; WO2006/52546; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 914942-88-4, 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 914942-88-4 as follows.

Dichlorobis(triphenylphosphine)rhoalladium (104mg, 0.145mmol) was added in one portion to a mixture of A1.12 (1.Og, 2.48mmol), 3-ethynyl-benzoic acid tert-butyl ester (753mg, 3.72mmol) and triethylamine (10ml) in DMF (7.0ml) at room temperature under a nitrogen atmosphere. The resulting mixture was heated to 90 0C for 50min before cooling to room temperature and evaporating in vacuo. The residue was purified by column chromatography using ethyl acetate:hexane as eluent to give 765mg (65%) of A72.1. Found: M+H = 478.21

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,914942-88-4, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2006/122137; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 89415-54-3 ,Some common heterocyclic compound, 89415-54-3, molecular formula is C6H8BrN3, 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.

A mixture of the 5-bromo-/V-methyl-3-nitro-2-pyridinamine (1.14 g, 4.21 mmol assumed). and ammonium chloride (1.103 g, 20.62 mmol) in EtOH^O (8.5 mL of a 1 :1 solution) was stirred as iron (1 .152 g, 20.62 mmol) was added. The mixture was heated to reflux for ~ 2 hours. The mixture was allowed to cool to room temperature then diluted with EtOH and filtered through Celite. The filtrate was concentrated to yield a black tar which was diluted with EtOH then concentrated three times. The residue was slurried in EtOH then filtered. The filtrate was concentrated to yield a black solid which was dissolved in pyridine (15.1 mL). N, N dimethylaminopyridine (0.060 g, 0.49 mmoL) was added followed bybenzenesulfonylchlonde (0.63 mL, 4.91 mmol). The resulting mixture was stirred for one hour under a nitrogen atmosphere. The mixture was then concentrated. The residue diluted with EtOAc, washed with water two times, then saturated NaHC03 followed by brine, dried(Na2S0 ) and concentrated. The residue was purified by silica gel chromatography (0-100% EtOAc in hexanes). Fractions containing the product were combined and concentrated to yield A/-[5-bromo-2-(methylamino)-3-pyridinyl]benzenesulfonamide (0.859 g, 2.51 mmol 60% over 3 steps) as a grey solid. 1H NMR (400 MHz, DMSO-d6) delta ppm 9.58 (br. s., 1 H) 7.94 (br. s., 1 H) 7.75 – 7.64 (m, 3 H) 7.62 – 7.55 (m, 2 H) 6.92 (d, J=2.3 Hz, 1 H) 6.25 (br. s., 1 H) 2.68 (d, J=4.5 Hz, 3 H) LCMS: m/z 344 (M+1 ).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,89415-54-3, its application will become more common.

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