Pyridine-derivatives

Electric Literature of 22245-83-6, 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 22245-83-6, name is 3-(Trifluoromethyl)pyridin-2-ol. This compound has unique chemical properties. The synthetic route is as follows.

Reference Example 117 5-nitro-3-(trifluoromethyl)pyridin-2-ol; 2-Hydroxy-3-(trifluoromethyl)pyridine (3.0 g) was added to conc. sulfuric acid (18 mL) under ice-cooling, and the mixture was stirred at the same temperature for 5 min. Fuming nitric acid (90-95%, 7 mL) was added dropwise over 5 min, and the mixture was allowed to return to room temperature over 2 hr, heated to 50 C. and stirred for 3 hr. After cooling to room temperature, the reaction mixture was poured into ice (200 g), and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The precipitate was washed with diisopropyl ether to give the title compound as a solid (yield 2.7 g, 69%). 1H-NMR (CDCl3) delta: 8.65-8.67 (1H, m), 8.80-8.81 (1H, m), 1H not detected.

According to the analysis of related databases, 22245-83-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Takeda Pharmaceutical Company Limited; US2007/60623; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 5398-44-7, 2,6-Dichloroisonicotinic 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, 5398-44-7, blongs to pyridine-derivatives compound. category: pyridine-derivatives

To a solution of 2,6-dichloroisonicotinic acid (10.0 g, 52.1 mmol) in THF (213 mL) at 0 0C was added dimethylaminopyridine (3.18 g, 26.0 mmol). A solution of di-tert-butyl dicarbonate (13.64 g. 62.5 mmol) in THF (20 mL) was added and the mixture was allowed to warm to ambient temperature. After 18 h, the solvent was removed and HCl (0.1 Nu aqueous solution) was added and the mixture was extracted with ethyl acetate (3x). The combined organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated: LC-MS [M+l-16] = 233.0.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5398-44-7, its application will become more common.

Reference:
Patent; MERCK SHARP &; DOHME CORP.; BURGEY, Christopher, S.; DENG, Zhengwu, J.; NGUYEN, Diem, N.; PAONE, Daniel, V.; POTTEIGER, Craig, M.; STAUFFER, Shaun, R.; SEGERDELL, Carolyn; NOMLAND, Ashley; LIM, John, J.; WO2010/111058; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 56026-36-9, 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.56026-36-9, name is Methyl 6-(hydroxymethyl)nicotinate, molecular formula is C8H9NO3, molecular weight is 167.16, as common compound, the synthetic route is as follows.

Dess-Martin periodinane (3.0 g, 7.2 mmol) was added slowly to the mixture of compound 38 (1.0 g,6.0 mmol) in DCM (10 mL). The resulting mixture continued to stir at room temperature overnight.The reaction was quenched with water. The aqueous phase was extracted with EtOAc. The combinedorganic phases were then processed in the usual way and chromatographed (3:1 petroleum ether/EtOAc)to yield compound 39 (0.85 g, 86%).

The chemical industry reduces the impact on the environment during synthesis 56026-36-9, I believe this compound will play a more active role in future production and life.

Reference:
Article; Wang, Wen-Long; Yang, Dong-Lin; Gao, Li-Xin; Tang, Chun-Lan; Ma, Wei-Ping; Ye, Hui-Hua; Zhang, Si-Qi; Zhao, Ya-Nan; Xu, Hao-Jie; Hu, Zhao; Chen, Xia; Fan, Wen-Hua; Chen, Hai-Jun; Li, Jing-Ya; Nan, Fa-Jun; Li, Jia; Feng, Bainian; Molecules; vol. 19; 1; (2014); p. 102 – 121;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 54415-77-9, Adding some certain compound to certain chemical reactions, such as: 54415-77-9, name is 1H-Pyrrolo[3,2-c]pyridin-4(5H)-one,molecular formula is C7H6N2O, 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 54415-77-9.

General procedure: A solution of 6,7-dimethoxyisoquinolin-1(2H)-one(200 mg, 0.97 mmol), phosphoryl trichloride (0.268 mL, 2.92 mmol) inacetonitrile (5 mL) was stirred at 110 C for 5 minutes under microwaveirradiation. The reaction was quenched with a saturated aqueous sodium bicarbonatesolution and stirred at ambient temperature for 1 h. It was filtered throughcelite and washed with ethyl acetate. The filtrate was concentrated to dryness.The crude material was purified by flash chromatography, eluting with heptanesand ethyl acetate (1:0 to 0:1) to give the desired product as a gum (99 mg,45.4 %).

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. 54415-77-9, 1H-Pyrrolo[3,2-c]pyridin-4(5H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Hu, Yun-Jin; St.-Onge, Miguel; Laliberte, Sebastien; Vallee, Frederic; Jin, Shujuan; Bedard, Leanne; Labrecque, Jean; Albert, Jeffrey S.; Bioorganic and Medicinal Chemistry Letters; vol. 24; 14; (2014); p. 3199 – 3203;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 31181-79-0, (3-Fluoropyrid-2-yl)methanol, 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, 31181-79-0, blongs to pyridine-derivatives compound. Formula: C6H6FNO

To a solution of (3-fluoropyridin-2-yl)methanol (1.80 g, 13.8 mmol, 1.0 equiv) in DCM (20 mL) was added SOCI2 (2.50 mL, 35.0 mmol, 2.5 equiv) dropwise at 0C. The resulting mixture was stirred at room temperature for 2 hours. The reaction mixture was quenched with saturated aqueous NaHCCb solution and extracted with DCM (3 * 20 mL). The combined organic layers were dried over anhydrous Na2S04 and concentrated in vacuo. The residue was purified by column chromatography (eluted with PE/EtOAc = 5/1) to afford 2-(chloromethyl)-3-fluoropyridine (1.33 g, 66% yield). LC-MS: m/z 146.0, 148.0 (M+H)+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,31181-79-0, its application will become more common.

Reference:
Patent; ANNAPURNA BIO, INC.; TANG, Haifeng; HANSON, Michael; BOYCE, Sarah; NIE, Zhe; (461 pag.)WO2020/73011; (2020); A1;,
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.13466-38-1, name is 5-Bromopyridin-2-ol, molecular formula is C5H4BrNO, molecular weight is 173.9954, as common compound, the synthetic route is as follows.COA of Formula: C5H4BrNO

To a solution of N-(4-(4-hydroxy-2,6-dimethylphenyl)-thiazol-2-yl)isonicotinamide (5-3, 325 mg, 1.0 mmol) in DMF (15 mL) were added cesium carbonate (650 mg, 2.0 mmol, 2.0 equiv) and Cu (19.5 mg, 0.30 mmol, 0.30 equiv). The mixture was stirred at 80-90 C for 60 min 5-Bromo-2-hydroxypyridine (261 mg, 1.5 mmol) was added to the solutionand the reaction mixture was stirred at 100 C for additional 24 hr. The solution was quenched with water (40 mL) and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography on (NH silica gel, hexane/ethyl acetate = 3/1-1/3) to give 5(0.75 g) in 18% yield: 1H NMR (500 MHz, CDCl3) delta 8.31 (d, J= 5.0 Hz, 2 H), 8.29 (d, J= 5.0 Hz, 2 H), 7.23 (d, J= 9.5 Hz, 1 H), 6.81 (s, 1H), 6.60 (d, J= 4.76 Hz, 1 H), 6.49 (s, 2 H), 5.42 (s, 1 H), 2.04 (s, 6 H), ESI-MS = m/z 417.2 (M – H)-.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,13466-38-1, 5-Bromopyridin-2-ol, and friends who are interested can also refer to it.

Reference:
Patent; TAIVEX THERAPEUTICS CORPORATION; HUANG, Yu-Ling; CHUANG, Shih-Hsien; LEE, Ying-Shuan Eda; HUANG, Jiann-Jyh; LAU, Johnson; WO2013/82324; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 125652-55-3, 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.125652-55-3, name is 1-Butyl-3-methylpyridinium Chloride, molecular formula is C10H16ClN, molecular weight is 185.69, as common compound, the synthetic route is as follows.

Example 91-Butyl-3-methylpyridinium dicyanodihydridoborate-[BMPy][BH2(CN)2]4.09 g (46.6 mmol) of sodium dicyanodihydridoborate, Na[BH2(CN)2], and 8.63 g (46.5 mmol) of 1-butyl-3-methylpyridinium chloride, [BMPy]Cl, are each dissolved in 20 ml of water and mixed. The product, 1-butyl-3-methylpyridinium dicyanodihydridoborate, [BMPy][BH2(CN)2], is extracted with 100+100+50 ml of CH2Cl2. The combined organic phases are washed with 50+50 ml of water, dried using Na2SO4, and the solvent is distilled off. [BMPy][BH2(CN)2] is dried at about 40 C. in vacuo for one day with stirring. The yield of 1-butyl-3-methylpyridinium dicyanodihydridoborate is 9.0 g (41.8 mol, 90%). 1H{11B}-NMR (solvent: acetone-D6; reference: TMS): delta, ppm=0.97 t (CH3, 3H), 3JH,H=7.5 Hz; 1.02 s (2H, BH2); 1.44 m (CH2, 2H); 2.08 m (CH2, 2H); 2.63 s (CH3, 3H), 4.71 t (CH2, 2H), 3JH,H=7.6 Hz; 8.08 d, d (CH, 1H), 3JH,H=7.0 Hz; 8.50 d (CH, 1H), 3JH,H=8.1 Hz; 8.88 d (CH, 1H), 3JH,H=6.1 Hz; 8.95 s (CH, 1H). 11B{1H}NMR (solvent: acetone-D6; reference: Et2O.BF3): delta, ppm=-41.7 s

The chemical industry reduces the impact on the environment during synthesis 125652-55-3, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Merck Patent GmbH; Ignatyev, Nikolai (Mykola); Schulte, Michael; Bernhardt, Eduard; Bernhardt-Pitchougina, Vera; Willner, Helge; US8927714; (2015); B2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 832735-56-5, 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.

A solution of 4-bromo-2-(difluoromethoxy)pyridine (1.25 g, 5.56 mmol) in 1,4-dioxane (30 mL) was added to Pd(dppf)Cl2(406 mg, 0.56 mmol), B2Pin2(1.55 g, 6.10 mmol) and KOAc (1.2 g, 12.2 mmol) under N2 and the reaction was heated to reflux for 22 h. The mixture was filtered through celite and concentrated in vacuo to afford the crude title compound (2.57 g) which was used without further purification.LCMS m/z 271.8 (M+H)+(ES+).1H NMR (DMSO-d6): d 8.28 (d, J = 4.9 Hz, 1H), 7.70 (t, J = 72.9 Hz, 1H), 7.41 (d, J = 4.8 Hz, 1H), 7.13 (s, 1H), 1.29 (s, 12H).

The chemical industry reduces the impact on the environment during synthesis 832735-56-5, I believe this compound will play a more active role in future production and life.

Reference:
Patent; INFLAZOME LIMITED; MILLER, David; MACLEOD, Angus; THOM, Stephen; MCPHERSON, Christopher G.; ALANINE, Thomas; CARRILLO ARREGUI, Jokin; CIANA, Claire-Lise; SHANNON, Jonathan; VAN WILTENBURG, Jimmy; DEN HARTOG, Jacobus Antonius Joseph; (603 pag.)WO2019/211463; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1603-40-3, 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. 1603-40-3, name is 3-Methylpyridin-2-amine. A new synthetic method of this compound is introduced below.

A. Preparation of (X) where Y and Z are Hydrogen A solution of 2-amino-3-methylpyridine (10.8 g) and di-tert-butyl dicarbonate (21.8 g) in tetrahydrofuran was heated under reflux for 12 hours. Evaporation afforded a solid which was recrystallized from ether-tetrahydrofuran to yield 2-(t-butoxycarbonylamino)-3-methylpyridine (10.2 g), a compound of Formula (X), m.p. 132-133 C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1603-40-3, 3-Methylpyridin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; Syntex (U.S.A.) Inc.; US5212195; (1993); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1060812-84-1, 5-Bromopyrazolo[1,5-a]pyridine, 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: C7H5BrN2, blongs to pyridine-derivatives compound. COA of Formula: C7H5BrN2

200 mg of compound 21 was suspended in 1 ml of sulfuric acid,Cool to 0 C. A 0.5 ml sulfuric acid / 0.5 ml nitric acid mixture was added dropwise, and the mixture was stirred at 0 C for 30 minutes. TLC detection,After the reaction, pour into ice water and stir for 10 minutes.160 mg of white solid was obtained by suction filtration.Used directly in the next reaction.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1060812-84-1, 5-Bromopyrazolo[1,5-a]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; Beijing Fulong Kangtai Biological Co., Ltd.; Ji Qi; Gao Congmin; Wang Lei; Gong Longlong; Chen Bo; Du Zhenjian; (21 pag.)CN110857304; (2020); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem