Category: pyridine-derivatives

504-29-0 , The common heterocyclic compound, 504-29-0, name is Pyridin-2-amine, molecular formula is C5H6N2, 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.

Manufacturing Example 39-1-1 2,2-Dimethyl-N-pyridin-2-yl-propionamide; To a solution of 2-aminopyridine (50.0 g, 531 mmol) in methylene chloride (500 mL) were added triethylamine (81.4 mL, 584 mmol) and pivaloyl chloride (71.9 mL, 584 mmol) at 0 C., which was stirred for 4 hours and 30 minutes at room temperature. The reaction solution was partitioned into water and methylene chloride. The organic layer was washed with water and saturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under a reduced pressure. To a solution of the resulting residue in methanol (300 mL) was added potassium carbonate (73.4 g, 531 mmol) at 0 C., which was stirred for 90 minutes at room temperature. The reaction solution was partitioned into water and ethyl acetate at room temperature. The organic layer was washed with saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate, and the solvent was evaporated under a reduced pressure. Heptane (300 mL) was added to the residue, and the precipitated solids were filtered to obtain the title compound (80.2 g, 85%). The filtrate was then concentrated under a reduced pressure, and the residue was purified by silica gel column chromatography (heptane:ethyl acetate=2:1) to obtain the title compound (12.2 g, 13%).1H-NMR Spectrum (DMSO-d6) delta (ppm): 1.22 (9H, s), 7.06-7.09 (1H, m), 7.72-7.77 (1H, m), 8.01-8.03 (1H, m), 8.29-8.31 (1H, m), 9.71 (1H, s).

According to the analysis of related databases, 504-29-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Tanaka, Keigo; Yamamoto, Eiichi; Watanabe, Naoaki; US2009/82403; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

17368-12-6, 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. 17368-12-6, name is 2-Chloro-4-hydroxypyridine. A new synthetic method of this compound is introduced below.

A mixture of 5-fluoro-4-methyl-2-nitropyridine (2 g, 12.81 mmol) and 2-chloro-4-hydroxypyridine (1.66 g, 12.81 mmol) in DMF (26 mL) was sparged with Ar, treated with K2CO3 (2.66 g, 19.22 mmol), heated at 88 C. for 24 h, then at 50 C. for 2 days. The mixture was treated with water and the resulting solid collected via filtration and dried to afford 5-((2-chloropyridin-4-yl)oxy)-4-methyl-2-nitropyridine (2.72 g, 80%). 1H NMR (400 MHz, DMSO-d6): delta 8.49 (s, 1H), 8.47 (s, 1H), 8.35 (d, J=5.7 Hz, 1H), 7.24 (d, J=2.3 Hz, 1H), 7.12 (dd, J=5.7, 2.3 Hz, 1H), 2.32 (s, 3H); MS (ESI) m/z: 266.0 (M+H+).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,17368-12-6, 2-Chloro-4-hydroxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; Deciphera Pharmaceuticals, LLC; Flynn, Daniel L.; Kaufman, Michael D.; Samarakoon, Thiwanka; Caldwell, Timothy Malcolm; Vogeti, Lakshminarayana; Ahn, YuMi; Patt, William C.; Yates, Karen M.; US2014/315917; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding some certain compound to certain chemical reactions, such as: 393-53-3, name is 3-Fluoroisonicotinic 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 393-53-3. 393-53-3

General Procedure: To a 50 mL round bottom flask equipped with a stir bar and a reflux condenser were added 3-fluoroisonicotinic acid (1.0 g, 7.09 mmol), methanol (10 mL) and sulfuric acid (4.2 mL). The reaction mixture was heated at 70 C overnight, cooled to room temperature and concentrated in vacuo. The residue was cooled in an ice bath, basified to pH 9 using saturated aqueous sodium carbonate and extracted with ethyl acetate (2x). The combined organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give the desired product as yellow oil (1.03 g, 94 %). 1H NMR (300 MHz, CDCl3): delta 8.62 (d, IH), 8.54 (d, IH), 7.77 (t, IH), 3.98 (s, 3H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 393-53-3.

Reference:
Patent; ASTRAZENECA AB; NPS PHARMACEUTICALS, INC.; WO2007/87135; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

74115-13-2, 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.74115-13-2, name is 5-Bromo-3-pyridinol, molecular formula is C5H4BrNO, molecular weight is 174, as common compound, the synthetic route is as follows.

General procedure for Mitsunobu Reaction (Method A). To a mixture of 5-Bromo-3- pyridinol (1.2 equiv) and Ph3P (1.6 equiv) in anhydrous THF taken in a flame-dried flask under N2, N-Boc protected alcohol (1 equiv) was added and the mixture was cooled to – 10 C. Diethyl azodicarboxylate (40% w/v) in toluene (1.6 equiv) was added dropwise to the mixture and was warmed gradually to the room temperature. After 48 h, the reaction mixture was quenched with 1 mL of water and the solvent was removed under reduced pressure. The resulting yellow oil was purified by column chromatography on silica gel to yield 55-60% as a white solid. Example 3(S)-tei”i-butyl-2-((5-bromopyridin-3-yloxy)methyl)azetidine-l-carboxylate (VMY-2-3): Method A was used. Yield 55% (white solid). 1H NMR (400 MHz, CDC13) ? 8.25 – 8.19 (m, 2H), 7.36 (s, 1H), 4.44 (d, J= 5.3, 1H), 4.32 – 4.20 (m, 1H), 4.06 (dd, J = 2.8, 10.1, 1H), 3.81 (t, J= 7.5, 2H), 2.36 – 2.14 (m, 2H), 1.36 (s, 9H). 13C NMR (100 MHz, CDC13 ) ? 156.07,155.41, 143.13, 136.65, 124.02, 120.28, 79.76, 69.00, 59.92,47.14, 28.37, 18.95.HRMS (ESI): exact mass calcd for Ci4Hi9BrN203 [M+H]+, 343.0657, found 343.0670.

Statistics shows that 74115-13-2 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-3-pyridinol.

Reference:
Patent; GEORGETOWN UNIVERSITY; DUKE UNIVERSITY; BROWN, Milton, L.; PAIGE, Mikell, A.; XIAO, Yingxian; KELLAR, Kenneth, J.; YENUGONDA, Venkata, Mahidhar; LEVIN, Edward, D.; REZVANI, Amir, H.; WO2013/71067; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

1990-90-5, 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. 1990-90-5, name is 3-Methylpyridin-4-amine, molecular formula is C6H8N2, 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 of intermediate 23d (100 mg) in CH2Cl2 (7 mL) were at 0 C. consecutively added N,N-diisopropyl ethylamine (140 muL), 3-methylpyridin-4-amine (40 mg) and bromotripyrrolidino phosphonium hexafluorophosphate (230 mg) and the resulting mixture was stirred at ambient temperature for 2 h. The volatiles were removed under reduced pressure and the residue was purified by column chromatography (Interchim cartridge 15SiHP/25 g, Cy/EtOAc) to yield the desired compound (84% yield). [0490] LC-MS (Method 2): m/z [M+H]+=341.1 (MW calc.=340.81); Rt=0.57 min.

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. 1990-90-5, 3-Methylpyridin-4-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Gruenenthal GmbH; Nordhoff, Sonja; Wachten, Sebastian; Kless, Achim; Voss, Felix; Ritter, Stefanie; US2014/194452; (2014); 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.13534-99-1, name is 2-Amino-3-bromopyridine, molecular formula is C5H5BrN2, molecular weight is 173.01, as common compound, the synthetic route is as follows.13534-99-1

Step 3. tert-butyl 4-(2-aminopyridin-3-yl)-2-fluorobenzoate A slurry of tert-butyl 2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (5.1 g, 15.83 mmol), 3-bromoaminopyridine (3.01 g, 17.41 mmol) and Pd(PPh3)4 (0.732 g, 0.633 mmol) in n-butanol (50 mL) and 2.0 M Na2CO3aqueous solution (19.79 mL, 39.6 mmol) was degassed, and then heated to 100¡ã C. overnight. The reaction was cooled, and diluted with ethyl acetate. The layers were separated, and the organics were washed with brine, filtered over celite and concentrated. The crude was purified by flash chromatography eluting with 10-50percent ethyl acetate/heptane to provide 3.41 g of tert-butyl 4-(2-aminopyridin-3-yl)-2-fluorobenzoate in 75percent yield.

Statistics shows that 13534-99-1 is playing an increasingly important role. we look forward to future research findings about 2-Amino-3-bromopyridine.

Reference:
Patent; Novartis AG; Bagdanoff, Jeffrey T.; Ding, Yu; Han, Wooseok; Huang, Zilin; Jiang, Qun; Jin, Jeff Xianming; Kou, Xiang; Lee, Patrick; Lindvall, Mika; Min, Zhongcheng; Pan, Yue; Pecchi, Sabina; Pfister, Keith Bruce; Poon, Daniel; Rauniyar, Vivek; Wang, Xiaojing Michael; Zhang, Qiong; Zhou, Jianguang; Zhu, Shejin; (366 pag.)US9242996; (2016); B2;,
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 13472-85-0, name is 5-Bromo-2-methoxypyridine. This compound has unique chemical properties. The synthetic route is as follows. 13472-85-0

XXV-6 was obtained following the synthetic scheme as described above. MS (ES) m/z (M+H) 231.95.

Statistics shows that 13472-85-0 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-2-methoxypyridine.

Reference:
Patent; INTERMUNE, INC.; RAMPHAL, Johnnie, Y.; BUCKMAN, Brad, Owen; EMAYAN, Kumaraswamy; NICHOLAS, John, Beamond; SEIWERT, Scott, D.; WO2015/153683; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

97483-77-7, 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. 97483-77-7, name is 5-Bromopicolinonitrile, molecular formula is C6H3BrN2, 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 mixture of 5- bromopicolinonitrile (3.0 g, 16.4 mmol) in MeOH (60 mL) was added di-tert-butyl dicarbonate (7.2 g, 32.8 mmol) and nickel chloride hexahydrate (0.33 g, 1.64 mmol). The mixture was cooled to 0C, followed by portion wise addition of NaBH4 (4.3 g, 0.115 mol) over 2 hr. The mixture was stirred at 15C for 1 hr then poured into ice- water (200 g) and extracted with EtOAc. The combined organic layers were washed with brine, dried over anhydrous Na2SC>4, and concentrated under reduced pressure. The residue was purified by flash column chromatography to give the desired product (2.2 g, 47% yield) as a yellow solid. LC-MS: m/z 287,289 (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. 97483-77-7, 5-Bromopicolinonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SPERO THERAPEUTICS, INC.; ZAHLER, Robert; (262 pag.)WO2016/112088; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

100-48-1, 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.100-48-1, name is Isonicotinonitrile, molecular formula is C6H4N2, molecular weight is 104.11, as common compound, the synthetic route is as follows.

70 g (1 mol) of hydroxyammonium chloride in 500 ml of methanol are introduced into the vessel, and a solution of 54 g (1 mol) of sodium methylate in 500 ml of methanol is added. After about 30 minutes, the sodium chloride is filtered off, 41.6 g (0.4 mol) of pyridine-4-carboxylic acid nitrile are added to the filtrate, and the batch is refluxed for 24 hours. Subsequently, the methanol is distilled off, and the residue is recrystallized from 2000 ml of isopropanol with simultaneously clarification with bleaching earth. 49.1 g (89.5% of th., relative to the nitrile used) of pyridine-4-amidoxime having a melting point of 207-208 C. are obtained which are reacted without further purification.

Statistics shows that 100-48-1 is playing an increasingly important role. we look forward to future research findings about Isonicotinonitrile.

Reference:
Patent; Hoechst Aktiengesellschaft; US4310665; (1982); A;,
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. 16133-25-8, name is Pyridine-3-sulfonyl chloride. This compound has unique chemical properties. The synthetic route is as follows. 16133-25-8

Weigh 1 mol of pyridine-3 sulfonyl chloride and 1 mol of 5-(2-fluorophenyl)-1H-pyrrole-3-carbaldehyde in an appropriate amount of acetonitrile solvent, and add 1 mol of an acid-binding agent, and the acid-binding agent is DMAP and The composition of sodium carbonate was uniformly stirred, heated to 60 C, and the temperature was raised to 1 C / min. The temperature was raised to 60 C and then incubated for 5 hours to carry out a nucleophilic substitution reaction. The reaction formula of the nucleophilic substitution reaction is as follows: As shown in the above reaction formula, the product of the nucleophilic substitution reaction is 5-(2-fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrole-3-carbaldehyde, said 5-(2- Fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrole-3-carbaldehyde is still present in the acetonitrile solvent. Next, the mixture after the above nucleophilic substitution reaction was allowed to stand for 3 h, and gradually cooled to room temperature.The mixture will undergo crystallization during the cooling process to form a solid-liquid mixture, and then the filtration operation is performed.The solid obtained after filtration is the nucleophilic substitution reaction product 5-(2-fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrole-3-carbaldehyde.It was dried, weighed, and converted to obtain 0.83 mol of 5-(2-fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrole-3-carbaldehyde.

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, 16133-25-8, Pyridine-3-sulfonyl chloride.

Reference:
Patent; Beijing Xinkaiyuan Pharmaceutical Technology Co., Ltd.; Li Jiahe; Wang Rui; Li Jing; Wu Yanpeng; Ge Zhimin; (24 pag.)CN109912568; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem