Pyridine-derivatives

Application of 1136-52-3, 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. 1136-52-3, name is (2,2,8-Trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-yl)methanol. A new synthetic method of this compound is introduced below.

General procedure: A mixture of alpha4,3-O-isopropylidene pyridoxine, the respective saccharideand molecular sieves (4 A) was stirred under argon atmospherein dry solvent (5 mL) at rt for 1 h before it was cooled to the respectivetemperature T. The promoter was added and the reaction mixture allowedto reach rt overnight. The mixture was diluted with dichloromethane(10 mL) and filtered through a pad of celite. Afterwards,the filtrate was washed with Na2S2O3 (10% in water, 30 mL) and theaqueous phase was extracted with dichloromethane (3 × 40 mL). Thecombined organic layers were washed with distilled water (1×50 mL),brine (1 × 50 mL) and dried over Na2SO4. The solvent was evaporatedunder reduced pressure and the crude product subjected to columnchromatography using SiO2 (pentane/ethyl acetate 1/1 to 1/4, gradientelution) followed by C18 (methanol, isocratic) to afford the glucoside.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1136-52-3, its application will become more common.

Reference:
Article; Bachmann, Thomas; Rychlik, Michael; Carbohydrate Research; vol. 489; (2020);,
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.832735-56-5, name is 4-Bromo-2-(difluoromethoxy)pyridine, molecular formula is C6H4BrF2NO, molecular weight is 224.0029, as common compound, the synthetic route is as follows.category: pyridine-derivatives

A mixture of C41 (120 mg, 0.467 mmol), C49 (105 mg, 0.469 mmol), tn’s(dibenzylideneacetone)dipalladium(0) (12.8 mg, 14.0 pmol), 4,5- bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos; 17.8 mg, 30.8 pmol), and cesium carbonate (608 mg, 1 .87 mmol) in 1 ,4-dioxane (5 mL) was stirred at 100 C for 16 hours. After cooling to room temperature, the reaction mixture was filtered, and the filtrate was concentrated in vacuo. The residue was purified using silica gel chromatography (Eluent: 20: 1 petroleum ether / ethyl acetate) to provide the product as a yellow oil. Yield: 50 mg, 0.17 mmol, 36%. 1 H NMR (400 MHz, CDCI3) delta 7.81 (d, J=5.9 Hz, 1 H), 7.42 (t, JHF=73.7 HZ, 1 H), 6.08 (dd, J=5.8, 2.1 Hz, 1 H), 5.75 (d, J=2.0 Hz, 1 H), 4.20-4.1 1 (m, 4H), 3.66 (dd, J=8.0, 5.5 Hz, 2H), 3.20-3.09 (m, 1 H), 2.71 (d, J=7.9 Hz, 2H), 1 .28 (t, J=7.1 Hz, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,832735-56-5, 4-Bromo-2-(difluoromethoxy)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; PFIZER INC.; ZHANG, Lei; BUTLER, Christopher Ryan; BECK, Elizabeth Mary; BRODNEY, Michael Aaron; BROWN, Matthew Frank; MCALLISTER, Laura Ann; LACHAPELLE, Erik Alphie; GILBERT, Adam Matthew; (170 pag.)WO2018/2760; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 56055-54-0, 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. 56055-54-0, name is Methyl 5,6-dichloronicotinate. A new synthetic method of this compound is introduced below.

Step B: Methyl 5-chloro-6- (2, 2, 2-trifluoro-1-methylethoxy) nicotinate; To a solution of 630 mg (3.06 mmol) of methyl 5,6-dichloronicotinate (from Step A) and 349 muL (3.06 mmol) of 1, 1, l-trifluoro-2-propanol in 10 mL of THF at-78 C was added 3.1 mL (3.06 mmol) of sodium bis (trimethylsilyl) amide (1.0 M in THF). After stirring at-78 C for 30 min and at 0 C for 5 h, the reaction was quenched by adding 10 mL of saturated NH4Cl. The mixture was poured into brine and extracted with CH2C12 (3 x 20 mL). Organic layers were combined, dried over MgS04, and concentrated. Chromatography on a Biotage 40M cartridge using 3: 97 v/v Et20/hexanes as the eluant gave 627 mg of the title compound : 1H NMR (500 MHz, CDC13) 8 1.56 (d, J = 6.4, 3H), 3.93 (s, 3H), 5.86 (m, 1H), 8.27 (d, J = 2.1, 1H), 8. 67 (d, J = 2.0, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,56055-54-0, Methyl 5,6-dichloronicotinate, and friends who are interested can also refer to it.

Reference:
Patent; MERCK & CO., INC.; WO2005/58848; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1008-91-9, 1-(Pyridin-4-yl)piperazine, 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, Computed Properties of C9H13N3, blongs to pyridine-derivatives compound. Computed Properties of C9H13N3

The crude material (1.15 g, 7.06 mmol) from Step B was dissolved in dichloromethane (50 mL). After addition of diisopropylethylamine (4.7 mL, 42.4 mmol), 3-nitrosali-cylic acid (1.94 g, 10.6 mmol), and PyBrOP (5.78 g, 12.3 mmol), the resulting mixture was stirred over night at room temperature before being put into IN sodium hydroxide (300 mL). Extraction with dichloromethane (2×100 mL) removed all PyBrOP products. The aqueous phase was carefully acidified to pH~5-6 with 3N HC1 and extracted with dichloromethane (3×100 mL). The combined organic layers of the neutral extraction were dried over sodium sulfate, concentrated, and finally purified by column chromatography (dichloromethane/methanol/NH4OH=10/l/0.1) to yield the desired product (850 mg, 37% for 2 steps).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1008-91-9, 1-(Pyridin-4-yl)piperazine, and friends who are interested can also refer to it.

Reference:
Patent; Schering Corporation and Pharmacopeia, Inc.; US2004/147559; (2004); 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. 15862-34-7, name is 5-Bromo-2-hydroxy-3-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C5H3BrN2O3

To a solution of 5-Bromo-3-nitro-pyridin-2-ol (10.0 g, 45.66 mmol) in 70 ml of toluene and 7 ml of DMF was added PBr3 (6.60 ml, 68.49 mmol) and the reaction mixture was heated at 12O0C for 20 min under nitrogen atmosphere. After the completion of the reaction mixture (TLC monitoring), water (100 mL) was added and extracted with ethyl acetate (3 x 200 mL). The combined organics was washed with water, brine, dried (Na2SO4), filtered and concentrated to get the desired product (10.30 g, 80.03%).

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; PROLYSIS LTD; WO2007/107758; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 499-51-4, 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 499-51-4 as follows.

A mixture of 205 4-hydroxypyridine-2,6-dicarboxylic acid 18a (10 g, 54.6 mmol), 206 phosphorus pentachloride (56 g, 272 mmol) and 179 chloroform (30 mL) was heated to 80 C. and stirred for three days. The mixture was cooled to room temperature and added slowly with 31 methanol (20 mL). The obtained mixture was stirred at room temperature for 2 h, basified with a solution of 118 sodium bicarbonate and extracted with dichloromethane (50 mL). The organic phase was combined, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to remove the solvent. The residue was purified by silica gel column chromatography to give the target 207 compound dimethyl 4-chloropyridine-2,6-dicarboxylate 18b (8 g, white solid). Yield: 64%. MS m/z (ESI): 230[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,499-51-4, its application will become more common.

Reference:
Patent; Beijing Innocare Pharma Tech Co., Ltd.; CHEN, Xiangyang; GAO, Yingxiang; US2019/185472; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 55717-45-8, Adding some certain compound to certain chemical reactions, such as: 55717-45-8, name is 6-Bromopyridin-3-ol,molecular formula is C5H4BrNO, 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 55717-45-8.

2-Bromo-5-hydroxypyridine (5 mmol) is dissolved in DMF (10 ml) and NaH (1.4 eq., 60% suspension in liquid paraffin) is added. After 30 min iodomethane (2 eq.) is added and the reaction solution is stirred 3 days. The reaction solution is pored into water and extracted with methyl-tert-15 butyl ether. The combined organic layers are dried over MgSO4 and the solvent is removed in vacuo. 2-Bromo-5-methoxy-pyridine is obtained as yellow oil in a yield of 79 %; HPLC (method C): 1.49 min; LC-MS (method A): 1.16 min, 187.95 (M+H+).

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. 55717-45-8, 6-Bromopyridin-3-ol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK PATENT GMBH; WO2009/46784; (2009); 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. 159503-91-0, name is tert-Butyl 4-bromo-5,6-dihydropyridine-1(2H)-carboxylate. This compound has unique chemical properties. The synthetic route is as follows. Formula: C10H16BrNO2

In the third step, a Grignard exchange reaction of 26.21 g (0.1 mol) of N-Boc piperidin-4-enyl bromide with 12.9 g (0.105 mol) of isopropyl bromide in tetrahydrofuran, and then, under the protection of nitrogen, At 0 C, 19.03 g (0.11 mol) of pinacol methoxyboronic acid was added dropwise to the Grignard reaction solution, the reaction was held for 4 h, and then the temperature was raised to reflux for 1 h. After the reaction was completed, 10 ml of 10% dilute hydrochloric acid was added to quench the reaction. After the solvent was distilled off, 120 ml of ethanol was added for beating. The white solid was filtered to obtain 26.9 g, and the yield was 87%.

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, 159503-91-0, tert-Butyl 4-bromo-5,6-dihydropyridine-1(2H)-carboxylate.

Reference:
Patent; Zhonghao (Dalian) Chemical Design Yuan Co., Ltd.; Wang Kewei; Cai Xiaochuan; Zhao Wenwu; Tang Peikun; Han Jianguo; (6 pag.)CN110526936; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 82671-06-5, 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 82671-06-5 as follows.

In a round-necked flask 2,6-dichloro-5-fluoro-nicotinic acid (20.0g, 95.2mmol), sodium methoxide (11.3g, 210mmol) and anhydrous methanol (with 260 mL of), the reaction was refluxed for 4 hours, cooled to at room temperature, was added 200mL of water, acidified with concentrated hydrochloric pH = 1, then extracted with ethyl acetate, dried over anhydrous Na2SO4Dried, the solvent was spin-product 19.0g, a yield of 97.4%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,82671-06-5, its application will become more common.

Reference:
Patent; Shandong Xuanzhu Pharmaceutical Technology co., LTD; WU, YONG QIAN; WANG, AI CHEN; (35 pag.)CN102887895; (2016); B;,
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. 1180132-17-5, name is 5-((4-Ethylpiperazin-1-yl)methyl)pyridin-2-amine, the common compound, a new synthetic route is introduced below. Recommanded Product: 1180132-17-5

Compound 8a (216 mg, 0.7 mmol), compound 12 (154 mg, 0.7 mmol), sodium carbonate (74 mg, 0.7 mmol), 4 5-bisdiphenylphosphino-9 9-dimethyloxanthene (Xantphos) , 121 mg, 0.21 mmol) dissolved in 1,4-dioxane (20 mL), added with palladium acetate (16 mg, 0.07 mmol) under nitrogen atmosphere, reacted at 90 C for 10 hours, and the reaction solution was cooled to room temperature. into 50 mL of water, extracted three times with dichloromethane (30mL x3), the organic phases were combined, dried over anhydrous sodium sulfate filtered, and spin dry solid was recrystallized from ethyl acetate to give a yellow solid T-1 (150 mg, 44%) .

The synthetic route of 1180132-17-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hangzhou Bai Cheng Pharmaceutical Technology Co., Ltd.; Sheng Rong; Lou Jinfang; Zhang Fengmin; Luo Jin; Wu Lijun; Yang Huan; Jin Zewu; Xiong Xiaohong; Qian Yang; (32 pag.)CN110156754; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem