Day: September 13, 2021

Adding a certain compound to certain chemical reactions, such as: 71690-05-6, 2,3-Dichloro-5-formylpyridine, 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: C6H3Cl2NO, blongs to pyridine-derivatives compound. Formula: C6H3Cl2NO

To a stirred slurry of methyltriphenylphosphonium bromide (10.0 g) in toluene (200 mL) at 0 C. was added potassium t-butoxide (3.07 g) portionwise to produce a yellow slurry. After 1 hr, the reaction mixture was cooled to -20 C. and 4 (4.0 grams, 22.72 mmol) dissolved in tetrahydrofuran (6 mL) was added dropwise to produce a purple colored slurry. The reaction mixture was heated to 0 C. and stirred for an additional 1 hr. Then the reaction mixture was treated with saturated aqueous brine (150 mL) and diluted with ethyl acetate (200 mL). The resulting organic portion was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting product was chromatographed by silica gel chromatography column eluting with a gradient of ethyl acetate (0%-10%)/hexanes to provide 2.77 g of 1 (70% yield). 1H NMR (400 MHz, CDCl3) delta 8:30 (1H, d, J=2.19 Hz), 7.80 (1H, d, J=2.19 Hz), 6.63 (1H, dd, J=10.96, 17.80 Hz), 5.86 (1H, d, J=17.80 Hz), 5.45 (1H, d, J=10.96 Hz). LC/MS (M+1): 174.

The synthetic route of 71690-05-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tafesse, Laykea; US2010/120862; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 66521-66-2, 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. 66521-66-2, name is 4-(Pyridin-3-yl)pyrimidin-2-amine, molecular formula is C9H8N4, 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 under nitrogen gas of 2-(3-methyl-4-bromobenzylamino)-3-cyano-4-(4-tert- butylaminopiperidin-1-yl)quinoline (190 mg, 0.376 mmol) in toluene (10 ml) was added 4-(pyridin- 3-yl)pyrimidin-2-amine (71 mg, 0.413 mmol) and t-BuONa (72 mg, 0.752 mmol). The resulting mixture was degassed 10 min with Argon gas, then Xantphos (21 mg, 0.0376 mmol) and Pd2(dba)3 (34 mg, 0.0376 mmol) were added and the reaction mixture was stirred at 100 °C for 1 h. The reaction mixture was then cooled to room temperature, filtered and concentrated under reduced pressure. The residue was partitioned between brine and EtOAc and the aqueous layer was extracted with EtOAc. The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure to give yellow oil. The crude compound which upon purification by flash chromatography using (silica-gel: 100-200 mesh, MeOH?CHCl3; 0:100? 20:80) gave 60 mg (yield 26percent) of an pale-yellow solid corresponding to 2-[4-(4-(pyridin-3- yl)pyrimidin-2-ylamino)-3-methylbenzylamino]-3-cyano-4-(4-tert-butylaminopiperidin-1- yl)quinoline. Mass:(ES+) C36H39N9 required 597; found 598 [M+H], HPLC/MS method 6

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 66521-66-2, 4-(Pyridin-3-yl)pyrimidin-2-amine.

Reference:
Patent; GENOSCIENCE PHARMA; BRUN, Sonia; BERET, Antoine; BASSISSI, Firas; HALFON, Philippe; COURCAMBECK, Jerome; (275 pag.)WO2017/191599; (2017); 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 131084-55-4, name is 5-Chloro-1H-pyrrolo[2,3-c]pyridine. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C7H5ClN2

5-Chloro-lH-pyrrolo[2,3-c]pyridine (400.0 mg, 2.614 mmol, 1.0 eq) was dissolved in DMF (20.0 mL). After cooling to 0 C, NIS (882 mg, 3.922 mmol, 1.5 eq) was added and the resulting mixture was stirred at rt for 18 h, then concentrated in vacuo. The resulting residue was purified by column chromatography to provide 5-chloro-3-iodo-lH- pyrrolo[2,3-c]pyridine (725 mg, ca 100%).

With the rapid development of chemical substances, we look forward to future research findings about 131084-55-4.

Reference:
Patent; LIFESCI PHARMACEUTICALS, INC.; MCDONALD, Andrew; QIAN, Shawn; (346 pag.)WO2018/11628; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1020253-15-9, 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.1020253-15-9, name is 4-Bromo-2-chloro-5-methoxypyridine, molecular formula is C6H5BrClNO, molecular weight is 222.47, as common compound, the synthetic route is as follows.

Step 105.2: 4-Bromo-5-methoxy-1-methyl-1 H-pyridin-2-one A solution of 4-bromo-2-chloro-5-methoxypyridine (1 g, 4.5 mmol) in dimethyl sulfate (1.9 mL, 19.5 mmol) was stirred at 120C for 16 h in a sealed tube. After cooling, acetonitrile and a saturated aqueous NaHC03 solution were added and the mixture was stirred at rt over week-end. DCM was added and extracted. The organic layer was dried (Na2S04), filtered and concentrated to give the title compound. tR: 0.57 min (LC-MS 2); ESI-MS: 218.0/220.0 [M+H]+ (LC-MS 2).

The chemical industry reduces the impact on the environment during synthesis 1020253-15-9, I believe this compound will play a more active role in future production and life.

Reference:
Patent; NOVARTIS AG; FURET, Pascal; GUAGNANO, Vito; HOLZER, Philipp; KALLEN, Joerg; LIAO, Lv; MAH, Robert; MAO, Liang; MASUYA, Keiichi; SCHLAPBACH, Achim; STUTZ, Stefan; VAUPEL, Andrea; WO2013/111105; (2013); 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. 86873-60-1, name is 5-Chloro-2-picolinic acid. This compound has unique chemical properties. The synthetic route is as follows. Safety of 5-Chloro-2-picolinic acid

B. 5-Chloropyridine-2-carbonyl chloride To a dry 250 mL round-bottom flask equipped with magnetic stirrer and reflux condenser was charged 5 g of 5-chloropyridine-2-carboxylic acid (0.0317 mol), 100 mL methylene chloride, and 5 drops of DMF as a catalyst. Some of the solid did not dissolve. Thionyl chloride (10 mL; 0.137 mol) was added in one portion, and the reaction was refluxed for a total of 7 hours. After cooling, the reaction was stripped to dryness and 5.1 g of a white solid was isolated. The NMR data is as follows: 300 MHz 1H NMR (CDCl3, TMS=0 ppm) 1.25 (t, 3H); 1.48 (s, 18H); 2.05 (d, 2H); 3.65 (t, 1H); 4.15 (q, 2H). The sample was stored in the refrigerator and had 59% isolated yield. The sample was used without additional purification and had 91% isolated 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, 86873-60-1, 5-Chloro-2-picolinic acid.

Reference:
Patent; DOW AGROSCIENCES LLC; US2009/253708; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 5435-54-1, 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. 5435-54-1, name is 3-Nitropyridin-4-ol. A new synthetic method of this compound is introduced below.

a) 4-Chloro-3-nitropyridine Phosphorus oxychloride (25 ml, 0.27 mol) was added to 4-hydroxy-3-nitropyridine (7.0 g, 50.0 mmol), followed by reaction at 80 to 90 C. for 1.5 hours. Phosphorus oxychloride was removed by distillation. About 100 g of ice was added to the residue, and 28% aqueous ammonia was added dropwise thereto to adjust the pH to 7. Then, 100 ml of water was added thereto, and the aqueous mixture was extracted three times with 200 ml of dichloromethane. The resulting dichloromethane layer was dried, and then dichloromethane was removed by distillation under reduced pressure to obtain 7.75 g of a yellow liquid (yield: 97.8%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,5435-54-1, 3-Nitropyridin-4-ol, and friends who are interested can also refer to it.

Reference:
Patent; The Green Cross Corporation; US5262415; (1993); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 73583-37-6, name is 4-Bromo-2-chloropyridine. A new synthetic method of this compound is introduced below., SDS of cas: 73583-37-6

The compound obtained in Step 1 670 mg (2.03 mmol) to 10 ml of 1,4-dioxane was dissolved in then PdCl2 (dppf) 2.CH2Cl2 163 mg (0.20 mmol) and 4-bromo-2-chloropyridine 1.16 g (6.09 mmol), 2M- sodium carbonate (Na2CO3) aqueous solution was added to 3.05 ml (6.09 mmol) was stirred under reflux at 110 for 4 hours. Celite (celite), filtered and concentrated under reduced pressure the filtrate was purified by silica gel column chromatography (dichloromethane: methanol = 3: 1, v / v) 380 to yield a target compound as a yellow solid in a yield of 60% mg (1.20 gained mmol)

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, 73583-37-6, 4-Bromo-2-chloropyridine.

Reference:
Patent; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; LEE, KYU YANG; IM, JAE CHO; LEE, BYUNG HO; OH, KWANG SEOK; KIM, JEONG YEONG; OH, SEUNG AE; LEE, JEONG HYUN; (38 pag.)KR2015/117319; (2015); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 50735-34-7, Adding some certain compound to certain chemical reactions, such as: 50735-34-7, name is Methyl 2-amino-5-bromopyridine-3-carboxylate,molecular formula is C7H7BrN2O2, 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 50735-34-7.

A mixture of methyl 2-amino-5-bromonicotinate (1 g, 4.33 mmol), 4,4,4′,4′,5,5,5′,5′- octamethyl-2,2′-bi(1,3,2-dioxaborolane) (1.319 g, 5.19 mmol), potassium acetate (1.274 g, 12.98 mmol) in dioxane (20 mL) was degassed (3 x) with vacuum/nitrogen.1,1′- Bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (0.353 g, 0.433 mmol) was added, and the mixture was degassed (2 x) and filled with N2. The reaction mixture was immersed in an oil bath at 80 C and stirred ON. The mixture was diluted with ethyl acetate, and washed with water and brine. The organic layer was collected, and the aqueous layers were sequentially extracted with ethyl acetate (2 x). The combined organic layers were dried over anhydrous sodium sulfate and concentrated. After purification by Biotage flash chromatography (40 g column; 0% – 100% ethyl acetate in hexane), the obtained product was triturated with ether to afford methyl 2- amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinate (0.6 g, 2.157 mmol, 49.8 % yield) as a light tan solid. (0645) MS ESI m/z 279.18 (M+H)

According to the analysis of related databases, 50735-34-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WATTERSON, Scott Hunter; ANDAPPAN MURUGAIAH SUBBAIAH, Murugaiah; DZIERBA, Carolyn Diane; GONG, Hua; GUERNON, Jason M.; GUO, Junqing; HART, Amy C.; LUO, Guanglin; MACOR, John E.; PITTS, William J.; SHI, Jianliang; VENABLES, Brian Lee; WEIGELT, Carolyn A.; WU, Yong-Jin; ZHENG, Zhizhen Barbara; SIT, Sing-Yuen; CHEN, Jie; (810 pag.)WO2019/147782; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 98549-88-3, 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.98549-88-3, name is 1H-Pyrrolo[2,3-b]pyridin-5-ol, molecular formula is C7H6N2O, molecular weight is 134.14, as common compound, the synthetic route is as follows.

1H-pyrrolo [2,3-b] pyridin-5-ol(1.20 g, 8.95 mmol, 1.03 eq) and methyl 2,4-difluorobenzoate (1.5 g, 8.71 mmol, 1.0 eq) were added to 20 mL of diethylene glycol dimethyl ether, followed by addition of potassium phosphate heptahydrate (3.5 G,14.0 mmol, 1.6 eq) under nitrogen atmosphere at 115 C overnight. TLC point plate analysis, as well as raw materials, most of which produce ortho products. TLC point plate analysis, as well as raw materials, add 0.3g 2,4-difluorobenzoic acid methyl ester and 0.5g potassium phosphate heptahydrate, continue to react overnight. And then TLC point board analysis, the effect is not very good, as well as raw materials. (30 mL × 3), the organic phase was dried with anhydrous sodium sulfate, spin-dried column, PE / EA (v / v) = 3/1 column, white Solid 525mg. Yield 22.2%.

Statistics shows that 98549-88-3 is playing an increasingly important role. we look forward to future research findings about 1H-Pyrrolo[2,3-b]pyridin-5-ol.

Reference:
Patent; Sunshine Lake Pharma Co.,Ltd.; Kou, Yuhui; Hu, Bolin; Jiang, Haigang; Ye, Jiuyong; Liu, Zhiqiang; Xie, Hongming; Zhang, Yingjun; (42 pag.)CN106565706; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 13534-98-0 , The common heterocyclic compound, 13534-98-0, name is 4-Amino-3-bromopyridine, 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.

A solution of intermediate 2 (1.12 g, 5.34 mmol), 4-amino-3-bromopyridine (0.924 g, 5.34 mmol), copper (I) iodide (102 mg, 0.534 mmol), triethylamine (3.59 mL, 25.8 mmol) and PdCl2(PPh3)2 (187 mg, 0.267 mmol) in DMF (9.24 mL) was purged by bubbling nitrogen. The mixture was stirred at 100 C overnight under N2. The mixture was cooled to rt and filtered through celite and the filtrate was kept. The celite plug was washed with EtOAc and the combined filtrates were washed with brine (3x), dried over MgS04, filtered and the volatiles were evaporated in vacuo. The crude material was purified on a 24 g Si02 gold column (elution with 0-5%> MeOH containing 2M NH3 over 7 min). The desired fractions were concentrated in vacuo to yield intermediate 6 as a light yellow solid (330 mg, 20%> yield).

The synthetic route of 13534-98-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BARTOLOME-NEBREDA, Jose, Manuel; TRABANCO-SUAREZ, Andres, Avelino; MARTINEZ VITURRO, Carlos, Manuel; TRESADERN, Gary, John; ALCAZAR-VACA, Manuel, Jesus; (126 pag.)WO2018/109198; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem