Day: January 12, 2021

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. 15862-34-7, name is 5-Bromo-2-hydroxy-3-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of 5-Bromo-2-hydroxy-3-nitropyridine

N,N’-dimethylformamide (3 mL) was added to a mixture of 5-bromo-2-hydroxy-3-nitropyridine (16.54 g, 80 mmol) and thionyl chloride (43 mL) and the mixture was stirred and heated to reflux. After 1 hour, the solution was cooled and the solvent was evaporated. The mixture was co-evaporated with toluene to give a dark solid. Purification by flash chromatography (10:1 hexanes/ethyl acetate) gave the title compound (14.63 g, 82%) as a yellow solid. 1H-NMR delta (CDCl3): 8.38 (d, J=3.0 Hz, 1H), 8.70 (d, J=3.0 Hz, 1H).

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, 15862-34-7, 5-Bromo-2-hydroxy-3-nitropyridine.

Reference:
Patent; Laboratorios Almirall, S.A.; EP2113503; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 55-22-1 , The common heterocyclic compound, 55-22-1, name is Isonicotinic acid, molecular formula is C6H5NO2, 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) 2-(4-Pyridinyl)benzoxazole A mixture of 2-aminophenol (10.9 g), isonicotinic acid (12.3 g) and polyphosphoric acid (250 g) is heated under a nitrogen atmosphere at 210 C. for 3 hours. The mixture is then cooled to 160 C. and slowly poured into 1 liter of water. The mixture is cooled by adding ice and neutralized with 50% sodium hydroxide solution yielding 16.2 g of crude product. Crystallization from hexane yields 14.8 g of the title compound, melting point 129-131 C.

The synthetic route of 55-22-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; E. R. Squibb & Sons, Inc.; US4169200; (1979); A;,
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.14254-57-0, name is Isonicotinoyl chloride, molecular formula is C6H4ClNO, molecular weight is 141.5551, as common compound, the synthetic route is as follows.HPLC of Formula: C6H4ClNO

General procedure: The appropriate acyl chloride (2.5 equiv) was added dropwise to a solution of triazolo[1,5-a]pyrimidin-2-amine 11 or 12 or triazolo[1,5-a]pyridin-2-amine 16 (1 equiv) in pyridine at 0 C. The reaction mixture was allowed to warm up to r.t. and stirred for 1-2 h. EtOAc was added, and the organic layer was washed with HCl 1N (2 X), followed by water or brine. After solvent evaporation, the resultant residue was treated with 7 N methanolic ammonia solution and stirred at r.t. overnight to hydrolyze any potential bis-acylated product formed. The product was then purified by flash chromatography on silica gel using as eluent a gradient of EtOAC (0 – 10%) in DCM or MeOH (0 – 5%) in DCM, washed with MeOH and dried in vacuum to afford the desired compound (adapted from 1).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,14254-57-0, Isonicotinoyl chloride, and friends who are interested can also refer to it.

Reference:
Article; Ribeiro, Carlos J.A.; Kankanala, Jayakanth; Xie, Jiashu; Williams, Jessica; Aihara, Hideki; Wang, Zhengqiang; Bioorganic and Medicinal Chemistry Letters; vol. 29; 2; (2019); p. 257 – 261;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 582325-22-2, 6-(3-Fluorophenyl)nicotinic acid, 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, Formula: C12H8FNO2, blongs to pyridine-derivatives compound. Formula: C12H8FNO2

To a vial was added, 6-(3-fluorophenyl)nicotinic acid (46.4 mg, 0.213 mmol), 1-(7,8-dihydro-5H-pyrano[4,3-d]pyrimidin-2-yl)piperidin-4-amine (50 mg, 0.21 mmol), EDAC (45.0 mg, 0.235 mmol), HOBT (28.8 mg, 0.213 mmol), and DMA (1 mL) followed by NMM (0.058 mL, 0.534 mmol). The reaction was stirred overnight at room temperature and then diluted with H20 and the resulting solid filtered and collected to give the desired product, N-(1-{5-[(2,5-dimethyl-2,5-dihydro-1H-pyrrol-1-yl)carbonyl]pyridin-2-yl}piperidin-4-yl)-6-(3-fluorophenyl)nicotinamide (81 mg, 88%). 1H NMR (400 MHz, DMSO-d6) ppm 9.06 (1 H, s), 8.45 (1 H, d, J=7.5 Hz), 8.21-8.30 (1 H, m), 8.04-8.14 (2 H, m), 7.89-8.02 (2H, m) 7.49-7.59 (1 H, m), 7.29 (1 H, t), 4.49-4.64 (5 H, m), 4.11 (1 H, br. s.), 3.89 (2 H, t, J=5.9 Hz), 2.94-3.07 (2 H, m), 1.88 (2 H, d, J=10.1 Hz), 1.42-1.56 (3 H, m). HRMS (TOF, ES+) calculated for M+H: 434.1992; observed 434.2165.

The synthetic route of 582325-22-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Blake, Tanisha D.; Hamper, Bruce C.; Huang, Wei; Kiefer, James R.; Moon, Joseph B.; Neal, Bradley E.; Olson, Kirk L.; Pelc, Matthew J.; Schweitzer, Barbara A.; Thorarensen, Atli; Trujillo, John I.; Turner, Steven R.; US2008/146569; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 13091-23-1, 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.13091-23-1, name is 4-Chloro-3-nitropyridine, molecular formula is C5H3ClN2O2, molecular weight is 158.54, as common compound, the synthetic route is as follows.

Procedure 14 Procedure 14 provides a preparation of 6-azaindazole-3-carboxlic acid from 4-chloro-3-nitropyridine. tert-Butyl ethyl propane-1,3-dioate (26.6 mmol) was added to a suspension of sodium hydride (1.11 g) in tetrahydrofuran (50.0 mL) at 0 C. The reaction mixture was allowed to warm to rt and was maintained for 30 min. The reaction mixture was then cooled to 0 C. and a solution of 4-chloro-3-nitropyridine (12.6 mmol) in tetrahydrofuran/N,N-dimethylformamide (9/1, 10 mL) was added dropwise. The mixture was allowed to warm to rt and was maintained for 1 h. The reaction was quenched with water (50 mL) and was neutralized with acetic acid to a pH of 5 (the color went from dark brown to yellow on neutralization). The mixture was extracted with ethyl acetate (50 mL) and the combined organic layers were washed with brine (25 mL), dried (magnesium sulfate), and concentrated to provide the product in 94% yield.

The chemical industry reduces the impact on the environment during synthesis 13091-23-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Schumacher, Richard; Danca, Mihaela Diana; Ma, Jianguo; Herbert, Brian; Nguyen, True Minh; Xie, Wenge; Tehim, Ashok; US2007/78147; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 929000-66-8, 3-Bromo-6-chloropyridine-2-carboxylic acid, 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, 929000-66-8, blongs to pyridine-derivatives compound. Recommanded Product: 3-Bromo-6-chloropyridine-2-carboxylic acid

Tosyl chloride (7.7 g, 40.4 mmol) was added to a solution of 2-chloro-5- bromo picolinic acid (4 g, 17 mmol) and pyridine (9.2 mL, 114 mmol) in 33 mL of t-BuOH at 00C. The reaction was then stirred at room temperature for 12 hours. NaHCO3 (Sat.) was then added and the mixture was extracted with ethyl acetate (3 times). The combined organic phases were washed with brine and dried over Na2SO4. Evaporation of the organic solvent afforded the desired compound 94A, which is used in the next step without further purification: 1H NMR (300 MHz, DMSO-d6) delta ppm 8.27 (1 H, d), 7.63 (1 H, d), 1.57 (9 H, s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,929000-66-8, its application will become more common.

Reference:
Patent; GENENTECH, INC.; THE WALTER AND ELIZA HALL INSTITUTE OF MEDICAL RESEARCH; ABBOTT LABORATORIES; BAELL, Jonathon, Bayldon; BUI, Chinh, Thien; COLMAN, Peter; CZABOTAR, Peter; DUDLEY, Danette, A.; FAIRBROTHER, Wayne, J.; FLYGARE, John, A.; LASSENE, Guillaume, Laurent; NDUBAKU, Chudi; NIKOLAKOPOULOS, George; SLEEBS, Brad, Edmund; SMITH, Brian, John; WATSON, Keith, Geoffrey; ELMORE, Steven, W.; HASVOLD, Lisa, A.; PETROS, Andrew, M.; SOUERS, Andrew, J.; TAO, Zhi-Fu; WANG, Le; WANG, Xilu; DESHAYES, Kurt; WO2010/80503; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1060811-62-2, 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. 1060811-62-2, name is 4,6-Dichloronicotinaldehyde. A new synthetic method of this compound is introduced below.

To a stirred solution of 2,6-difluoro-3,5-dimethoxyaniline (9.03 g, 47.7 mmol), sodium triacetoxyborohydride (38.0 g, 180 mmol) in methylene chloride (60 mL)/ trifluoroacetic acid (30. mL), 4,6-dichloronicotinaldehyde (8.00 g, 45.5 mmol) was added in small portions at room temperature. After 1 hour, the volatiles were removed in vacuo and saturated aqueous NaHCO3 (200 mL) was added. The resulting mixture was extracted withDCM (3 xl 50 mL). The organic layers were combined, dried over Na2SO4, and concentrated. The residue was purified on silica gel (eluting with 0 to 0-40percent EtOAc in hexanes) to affordthe desired product (15.0 g). LC-MS calculated for C14H13C12F2N202 [M+H] mlz: 349.0; found 349.1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1060811-62-2, 4,6-Dichloronicotinaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; INCYTE CORPORATION; LU, Liang; SHEN, Bo; SOKOLSKY, Alexander; WANG, Xiaozhao; WU, Liangxing; YAO, Wenqing; YE, Yingda; (217 pag.)WO2016/134320; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 918511-92-9, 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.918511-92-9, name is 5-(Pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine, molecular formula is C12H9N3, molecular weight is 195.22, as common compound, the synthetic route is as follows.

To propane-2-sulfonic acid (2,4-difluoro-3-formyl-phenyl)-amide (60, 220.0 mg, 0.83 mmol) in methanol (15 niL) was added 5-pyridin-3-yl-lH-pyrrolo[2,3-b]pyridine (89, 150.0 mg, 0.77 mmol, prepared as described in Example 17) and potassium hydroxide (537.0 mg, 9.6 mmol) under an atmosphere of nitrogen. The reaction was stirred at room temperature overnight. The reaction was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and filtrated. The filtrate was concentrated and purified by silica gel column chromatography eluting with 5% methanol in dichloromethane to give the compound (61, 160 mg, 45.3%). In this step, minor compound Propane-2-sulfonic acid {2,4-difiuoro-3-[methoxy-(5-pyridin- 3-yl-lH-pyrrolo[2,3-b]pyridin-3-yl)-methyl]-phenyl}-amide was also formed and isolated. MS(ESI) [M + H+J+= 460.1.

The chemical industry reduces the impact on the environment during synthesis 918511-92-9, I believe this compound will play a more active role in future production and life.

Reference:
Patent; PLEXXIKON, INC.; WO2007/2325; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1221398-11-3, 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. 1221398-11-3, name is 6-Chloro-5-iodopyridin-2-amine. A new synthetic method of this compound is introduced below.

Potassium phosphate (12.72 g, 60 mmol), triphenyl phosphine (0.682 g, 2.40 mmol), 6-chloro-5-iodo-2-aminopyridine (6.1 g, 24 mmol), 2-methoxybenzeneboronic acid (5.10 g, 33.5 mmol) and palladium acetate (0.27 g, 1.20 mmol) were sequentially added to degassed acetonitrile (200 mL) and water (60 mL) under nitrogen. The reaction mixture was heated at 75 C. for overnight, then cooled to room temperature. The organic layer was separated and aqueous layer and was extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, concentrated and purified by silica column using hexanes and ethyl acetate as eluent furnishing 4.05 g of title compound. Synthesis of 2-chlorobenzofuro[2,3-b]pyridine:

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1221398-11-3, its application will become more common.

Reference:
Patent; UNIVERSAL DISPLAY CORPORATION; US2012/61654; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 79055-62-2, Adding some certain compound to certain chemical reactions, such as: 79055-62-2, name is 2-Chloro-5-methylpyridin-4-amine,molecular formula is C6H7ClN2, 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 79055-62-2.

To a mixture of tert-butyl nitrite (150 mL, 1262 mmol) in acetonitrile (1000 mL) was added copper(II) bromide (226 g, 1010 mmol) at 30 C. The solution was then stirred at 22 C for 40 min and then cooled to 0 C. A solution of 2-chloro-5-methylpyridin-4-amine (120 g, 842 mmol) in acetonitrile (500 mL) was added at 0 C. The reaction was stirred at 0 C for 1 h and then warmed to 22 C and stirred for 12 h. The resulting mixture was concentrated in vacuum. The residue was dissolved in DCM (2000 mL), washed with aqueous NH3 (15%, 2000 mL), dried over anhydrous Na2S04, and filtered. The filtrate was concentrated in vacuum and the resulting residue was purified by flash silica gel chromatography (eluting with ethyl acetate/pet. ether gradient) to give 4-bromo-2-chloro-5-methylpyridine as colorless oil. MS: 206 / 208 (M + 1 / M + 3). 1H MR (400 MHz, CDC13) delta 8.14 (s, 1H), 7.48 (s, 1H), 2.30 (s, 3H).

According to the analysis of related databases, 79055-62-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; CTXT PTY. LTD.; MACHACEK, Michelle, R.; WITTER, David, J.; REUTERSHAN, Michael Hale; ALTMAN, Michael, D.; STUPPLE, Paul Anthony; (67 pag.)WO2019/94311; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem