Category: pyridine-derivatives

Adding a certain compound to certain chemical reactions, such as: 588729-99-1, 3-Amino-5-bromo-2-chloropyridine, 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, COA of Formula: C5H4BrClN2, blongs to pyridine-derivatives compound. COA of Formula: C5H4BrClN2

EXAMPLE 32; N-(2-chloro-5-(4-(4-morpholinyl)-6-quinolinyl)-3-pyridinyl)-2- fluorobenzenesulfonamide; (l)2-chloro-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyridin-3- amine.; (Some starting materials may be obtained from Aldrich, St. Louis, MO) To a 5 ml microwave tube was added 5-bromo-2-chloropyridin-3-amine (0.1 g, 0.5 mmol), bis(pinacolato)diboron (0.2 g, 0.7 mmol), potassium acetate (0.2 g, 2 mmol), 1,1′- bis(diphenylphosphino)ferrocene]dichloride palladium(ii) (0.03 g, 0.04 mmol), and dioxane (3 mL). The vial was sealed and placed in Biotage Initiator microwave (Biotage, Charlottesville,VA) for 20 min at 110 0C. LC/MS showed no sign of starting material. Dioxane was removed in vacuo. The residue was partitioned between EtOAc/water. The organic layer was washed with water, brine, dried over MgSO4 and removed solvent. The crude product was purified using SiO2 (12g) chromatography with hexanes_acetone=85%: 15% as the solvent system to afford the desired product as light yellow solid (75 mg). A peak at 38 min was collected. The solvent was concentrated to afford the desired product as light yellow solid (75 mg). MS (ESI pos. ion) m/z: calc’d for CHH16BCIN2O2: 254.1; found: 255.3 (M+l). 1H NMR (300 MHz, CHL0R0F0RM- d) delta ppm 1.35 (s, 12 H) 4.03 (br. s., 2 H) 7.40 (d, J=1.61 Hz, 1 H) 8.14 (d, J=1.61 Hz, 1 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,588729-99-1, 3-Amino-5-bromo-2-chloropyridine, and friends who are interested can also refer to it.

Reference:
Patent; AMGEN INC.; WO2009/155121; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 13534-97-9 ,Some common heterocyclic compound, 13534-97-9, molecular formula is C5H5BrN2, 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.

Step 1; To a solution of 2-bromo-5-aminopyridine (3 g, 17.3 mmol) and potassium thiocyanate (4.2 g) in acetic acid (20 mL), bromine (3.3 g) was added dropwise under icebath-cooling. The solution was then stirred for 1 hour and subsequently at 100°C overnight. After the reaction mixture was cooled, water was added thereto. The precipitate was collected by filtration, then subjected to a next reaction without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13534-97-9, its application will become more common.

Reference:
Patent; Shionogi & Co., Ltd.; EP2426135; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 5470-70-2 ,Some common heterocyclic compound, 5470-70-2, molecular formula is C8H9NO2, 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.

Iodine (33.5g, 0.13mmol) and trifluoroacetic acid (35.3ml, 0.4mmol) were added to a solution of methyl 6-carboxylate-1-picoline (20g, 0.13mol) in N,N-dimethylsulfoxide (200ml) at 0°C and the mixture was stirred for 1 hourand then heated to 140°C and stirred for 2.5 hours. After being cooled to 0°C, the reaction was quenched with saturatedsodium thiosulfate solution (30ml) and stirred for 30 minutes. The aqueous layer was extracted with ethyl acetate (150ml3 3) and the organic layers were combined and washed with brine (50ml 3 2), dried over anhydrous sodium sulfate,filtered, concentrated in vacuo and the residue was purified by flash silica gel column chromatography to give the titlecompound (8g, yield 37percent). 1H NMR (400MHz, CHLOROFORM-d) ppm :10.14 (s, 1H), 9.36 (s, 1H), 8.47 (dd, J=1.3, 8.0Hz, 1H), 8.03 (d, J=8.0 Hz, 1H), 4.05 – 3.94 (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,5470-70-2, its application will become more common.

Reference:
Patent; Harbin Zhenbao Pharmaceutical Co., Ltd.; Medshine Discovery Inc.; CHEN, Shuhui; CHEN, Zhengxia; DAI, Meibi; XIE, Cheng; LI, Peng; ZHANG, Yang; LIANG, Guibai; WANG, Qiang; LIAO, Jiangpeng; SUN, Fei; HU, Guoping; LI, Jian; (166 pag.)EP3333157; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 153034-82-3, 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.153034-82-3, name is 2-Fluoro-4-iodonicotinaldehyde, molecular formula is C6H3FINO, molecular weight is 250.997, as common compound, the synthetic route is as follows.

To a stirred solution of 2-fluoro-4-iodopyridine-3- carboxaldehyde (10.Og5 39.8 rnmol) in tert-butanol (350 mL) and water (100 niL) at room temperature were added 2-methyl-2-butene (42.1 ml, 398 mmol), sodium phosphate, monobasic, monohydrate (60.5 g, 438 mmol) and sodium chlorite (18.0 g, 199 mmol). The reaction mixture was stirred at room temperature for 75 min. The reaction mixture was diluted with dichloromethane and a 6M aqueous solution of hydrochloric acid was added until pH ~2. EPO T/US2006/016344The water layer was extracted with dichloromethane. The organic phase was dried over MgSO4, filtered and concentrated in vacuo. Purification by MPLC (CH2Cl2MeOH+ 1% AcOH: 100/0 to 80/20) afforded 2-fluoro-4-iodonicotinic acid (10.63 g, 39.8 mmol, 100% yield). MS (ESI pos. ion) m/z: 268 (MH+). Calc’d exact mass for C6H3FINO2: 267.

Statistics shows that 153034-82-3 is playing an increasingly important role. we look forward to future research findings about 2-Fluoro-4-iodonicotinaldehyde.

Reference:
Patent; Amgen Inc.; WO2006/116713; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1124382-72-4 ,Some common heterocyclic compound, 1124382-72-4, molecular formula is C6H5BrN4, 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 8-bromo-[1,2,4]triazolo[1,5-a]pyridine-2-ylamine (35a) (10 g, 45 mmol), 4-fluoro-phenylboronic acid (12.61 g, 89 mmol), [1,1?-bis(diphenylphosphino)ferrocene] dichloro palladium(II) (2.93 g, 4 mmol) and sodium carbonate solution (2N in water, 44.6 mL, 89 mmol) in 1,4-dioxane (200 mL) was stirred at 110C under nitrogen atmosphere for 12h. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic phase was dried over Na2SO4 and concentrated under reduced pressure. The remainder was purified by preparative MPLC (silica gel, PE/ethyl acetate 20:1) to afford the product (36a). Yield: 8.6 g (80%). LCMS (ESI+) calculated for C12H9FN4 [M + H]+ m/z 229.0889, found 229.1. 1H NMR (400 MHz, (CD3)2SO) delta 8.54 (dd, J = 6.7, 1.0 Hz, 1H), 8.14-8.21 (m, 2H), 7.70 (dd, J = 7.3, 1.0 Hz, 1H), 7.29-7.37 (m, 2H), 6.97 (dd, J = 7.3, 6.7 Hz, 1H), 6.12 (s, 2H). TLC (silica gel, PE/ethyl acetate 10:1): Rf = 0.5. HPLC (method 3) Rt = 0.43 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1124382-72-4, its application will become more common.

Reference:
Article; Gerlach, Kai; Hobson, Scott; Eickmeier, Christian; Gross, Ulrike; Braun, Clemens; Sieger, Peter; Garneau, Michel; Hoerer, Stefan; Heine, Niklas; Bioorganic and Medicinal Chemistry; vol. 26; 12; (2018); p. 3227 – 3241;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 178876-82-9, 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. 178876-82-9, name is Methyl 6-amino-5-bromopicolinate, molecular formula is C7H7BrN2O2, 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.

To a solution methyl 6-amino-5-bromopyridine-2-carboxylate (20.04 g) in acetic acid (900 ml) was added N-chlorosuccinimide (13.96 g) and the resultant solution was heated to 120C for 1 hour. The solution was then evaporated and treated with excess aqueous sodium bicarbonate and extracted with dichloromethane. The organic fraction was dried and evaporated to give the product (21. 98 g). MS (+ve ion electrospray) mlz 265 and 267 (MH+, 100%)

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 178876-82-9, Methyl 6-amino-5-bromopicolinate.

Reference:
Patent; SMITHKLINE BEECHAM P.L.C.; WO2003/87098; (2003); 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. 944937-53-5, name is 6-Bromo-1H-pyrrolo[3,2-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows. Safety of 6-Bromo-1H-pyrrolo[3,2-b]pyridine

To a solution of 6-Bromo-lEta-pyrrolo[3,2- b]pyridine (1.9 g, 10 mmol) in 20 mL of DMF at 00C was added NaH (60% in oil, 0.49 g, 12 mmol) in three portions. The mixture was stirred at room temperature for 30 min. A solution of NH2Cl in Et2O (prepared according to the procedure described in J. Org. Chem. 2004, 1371 : -0.15 M, 80 mL) was added at -200C. The mixture was warmed up to room temperature for 15 min and was poured into a saturated solution of thiosulfate and ammonium chloride, and extracted with ethyl acetate. The organic layer was concentrated and the residue washed with small amount of ethyl acetate to give pink solid (1.3 g, 62% 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, 944937-53-5, 6-Bromo-1H-pyrrolo[3,2-b]pyridine.

Reference:
Patent; ARIAD PHARMACEUTICALS, INC.; QI, Jiwei; WANG, Yihan; LI, Feng; SHAKESPEARE, William, C.; KOHLMANN, Anna; DALGARNO, David, C.; ZHU, Xiaotian; WO2010/68292; (2010); 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. 626-05-1, name is 2,6-Dibromopyridine, molecular formula is C5H3Br2N, 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. Recommanded Product: 626-05-1

General procedure: Into a 25 mL round-bottomed flask were added Pd(PPh3)2Cl2 (0.06 g, 2.0 mol %), 2,6-dibromopyridine (0.60 g, 2.5 mmol) and 5.0 mL of 4-(ethoxycarbonyl)-phenylzinc bromide (0.5 M in THF, 2.5 mmol) under an argon atmosphere at room temperature. The resulting mixture was stirred at room temperature for 0.5 h. Quenched with saturated NH4Cl solution, then extracted with ethyl ether (10 mL × 3). Washed with saturated NaHCO3, Na2S2O3 solution and brine, then dried over anhydrous MgSO4. Purification by column chromatography on silica gel (10% ethyl acetate/90% heptane) afforded 0.31 g of 3a in 50% isolated yield as a white solid.

With the rapid development of chemical substances, we look forward to future research findings about 626-05-1.

Reference:
Article; Jung, Hye-Soo; Kim, Seung-Hoi; Bulletin of the Korean Chemical Society; vol. 35; 1; (2014); p. 280 – 282;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 17282-40-5, 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. 17282-40-5, name is 1-(2-Ethoxy-2-oxoethyl)pyridin-1-ium bromide. A new synthetic method of this compound is introduced below.

General procedure: A mixture of 4-hydroxy-6-methyl-2H-pyran-2-one (100 mg, 0.786 mmol), benzyl amine (84 mg, 0.786 mmol) in EtOH (5 mL), was stirred at room temperature for 5 min. Then benzaldehyde (83 mg, 0.147 mmol), pyridinium ylide (193 mg, 0.786 mmol), triethylamine (8 mg, 0.786 mmol) added sequentially to the mixture and it was refluxed at 80 C for 20 min till the completion of the reaction (monitored by TLC). After completion of reaction ethanol was distilled out and in the product crushed ice (25 g) was added. To this 0.5 MHCl (1 mL) was added and the resulting aqueous with suspended solids was extracted with dichloromethane (2 × 10 mL) and concentrated. Crude product was purified through column chromatography by eluting with hexanes and EtOAc mixtures (TLC, 45 % EtOAc in hexanes; Rf = 0.34). After recrystallization from EtOH, product obtained as light yellow colour crystalline solid;

At the same time, in my other blogs, there are other synthetic methods of this type of compound,17282-40-5, 1-(2-Ethoxy-2-oxoethyl)pyridin-1-ium bromide, and friends who are interested can also refer to it.

Reference:
Article; Tangeti, Venkata Swamy; Reddy, Boyi Harika; Evangeline, K. Sharon; Asian Journal of Chemistry; vol. 30; 2; (2018); p. 403 – 410;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 68470-59-7 , The common heterocyclic compound, 68470-59-7, name is 2-(Bromomethyl)-6-methylpyridine, molecular formula is C7H8BrN, 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.

[2-chloro-5-[(E)-N-hydroxy-C-methyl-carbonim idoyl]phenyl]methyl N-methylcarbamate (500 mg, 1 .9 mmol) and 2-(bromomethyl)-6-methylpyridine (720 mg, 3.9 mmol) were dissolved in dimethyl formamide (DMF) (35 mL). Then K2C03 (810 mg, 5.8 mmol) was added and themixture was stirred at room temperature overnight. After the addition of water, the solution was extracted with EtOAc and the organic layer was dried over Na2SO4. Concentration and purification by preparative H PLC yielded in [2-chloro-5-[(E)-C-methyl-N-[(6-methyl-2- pyridyl)methoxy]carbonimidoyl]phenyl]methyl N-methylcarbamate (190 mg, 28%) as a pale white solid and in its Z-isomer (160 mg, 23%) as a white solid.

The synthetic route of 68470-59-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BASF SE; WINTER, Christian; RHEINHEIMER, Joachim; WOLF, Antje; POONOTH, Manojkumar; TERTERYAN, Violeta; WIEBE, Christine; KREMZOW-GRAW, Doris; ROeHL, Franz; GRAMMENOS, Wassilios; ROHRER, Sebastian Georgios; WIEJA, Andy; ROSENBAUM, Claudia; WO2014/207071; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem