Pyridine-derivatives

Electric Literature of 61338-13-4, 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 61338-13-4, name is 2-(4-Methyl-2-phenylpiperazin-1-yl)nicotinic acid. This compound has unique chemical properties. The synthetic route is as follows.

Stirring blade,In a 1 L three-necked flask equipped with a thermometer, 60 g (201.8 mmol) of the pyridine carboxylic acid compound was suspended in 270 mL of tetrahydrofuran,It was cooled to 10 C.Under nitrogen flow70% sodium bis (2-methoxyethoxy) aluminum hydrideOf a toluene solution240 g (706.2 mmol) was added dropwise,The reaction was carried out at 40 C. for 5 hours.After completion of the reaction,The reaction solution was cooled to 10 C.,The reaction solution was added to 275 mL of a 35% by mass Rochelle salt aqueous solution cooled to 10 C. with stirring for 5 minutes.The temperature of the mixed solution at this time was 15 C.In addition, precipitation of aluminum hydroxide was not confirmed.Thereafter, the mixture was stirred for 10 minutes, and an organic layer and an aqueous layer were separated.The organic layer was concentrated under reduced pressure to obtain a pyridine methanol compound as a residue.240 mL of diethyl ether was added to the residue, and the mixture was stirred at room temperature for 30 minutes to obtain a crystallized pyridine methanol compound.After filtering the crystals,Dried under reduced pressure at 40 C. for 5 hours,Pyridine methanol compound (51 g).(Yield 89%, purity 99.3%, excess reductant amount 0.2%).

According to the analysis of related databases, 61338-13-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TOKUYAMA CORPORATION; KASAI, SOKO; MIYAOKU, TAKAYUKI; (10 pag.)JP2017/154976; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 33252-64-1, 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. 33252-64-1, name is 3-Nitro-5-(trifluoromethyl)pyridin-2(1H)-one. A new synthetic method of this compound is introduced below.

3-Nitro-5-(trifluoromethyl)pyridin-2-ol (31.00 g, 149 mmol) was dissolved in acetonitrile (250 ml) to give a dark brown solution. Phosphorus(V) oxybromide (85 g, 298 mmol) was added and the mixture was heated at reflux for 4 hours and then stirred at RT overnight. The reaction mixture was quenched by pouring into vigorously stirring water (600 ml) containing sodium hydrogencarbonate (1 10 g). The dark brown mixture was extracted with DCM (3 x 200 ml) and the organic phase was washed with water (200 ml) and brine (100ml), dried (MgS04) and concentrated under reduced pressure to afford the title product as a brown oil. H-NMR: [400MHz, CDCI3, ? 8.87 (1 H, d, J = 1.4Hz, ArH), 8.39 (1 H, d, J = 1 .9Hz, ArH).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,33252-64-1, 3-Nitro-5-(trifluoromethyl)pyridin-2(1H)-one, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; LEGRAND, Darren Mark; WO2013/38373; (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. 1121-76-2, name is 4-Chloropyridine 1-oxide. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 4-Chloropyridine 1-oxide

4-Chloropyridine-N-oxide (3.0 g, 23 mmol), 4-trifluoromethylphenylboronic acid (6.57 g, 34.6 mmol), K2CO3 (4.8 g, 35 mmol) and PdCl2(dppf) (470 mg, 0.57 mmol) were stirred in DMSO (40 mL) under vacuum for 30 min. The flask was flushed with nitrogen, and the mixture was heated to 80 C. for 10 min. Upon cooling, the mixture was diluted with methylene chloride and washed with 5% lithium chloride solution (5*), dried, concentrated, and the residue was purified by flash column chromatography (40 g ISCO column eluting with methylene chloride and a methanol/ammonia mixture (10:1); gradient 100% methylene chloride to 80% methylene chloride over 30 min at 40 mL/min) to provide the title compound (1.90 g, 34%) as a tan solid: ESI MS m/z 240 [M+H]+.

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, 1121-76-2, 4-Chloropyridine 1-oxide.

Reference:
Patent; ALBANY MOLECULAR RESEARCH, INC.; US2012/157460; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 144100-07-2 ,Some common heterocyclic compound, 144100-07-2, molecular formula is C5H3BrFN, 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 mixture of 2-bromo-6-fluoropyridine (212 mg, 1.21 mmol), (R)-1-(tetrahydro-2H- pyran-4-yl)ethanamine (200 mg, 1.21 mmol), DIPEA (187 mg, 1.45 mmol) and DMSO (3 ml_) was heated in a sealed tube at 90 °C for 18 hrs. The reaction mixture was allowed to cool to room temperature, poured into water (30 ml_) and stirred for 20 min. The mixture was extracted with EtOAc (3x 15 ml_). The combined organic layers were washed with brine (100 ml_) and concentrated to dryness under reduced pressure. The residue was purified by column chromatography [silica gel] providing (R)-6-bromo-N-(1- (tetrahydro-2H-pyran-4-yl)ethyl)pyridin-2-amine (290 mg). LCMS (m/z): 285.0/286.9 [M+H]+; Rt = 0.91 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,144100-07-2, its application will become more common.

Reference:
Patent; NOVARTIS AG; BARSANTI, Paul A.; HU, Cheng; JIN, Xianming; NG, Simon C.; PFISTER, Keith B.; SENDZIK, Martin; SUTTON, James; WO2012/101063; (2012); A1;,
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. 183610-70-0, name is 2-Amino-3-(trifluoromethyl)pyridine. A new synthetic method of this compound is introduced below., name: 2-Amino-3-(trifluoromethyl)pyridine

To a solution of 5.37 g (32.8 mmol) of 3-trifluoromethyl-pyridin-2-ylamine (Fluorochem Ltd., Derbyshire, United Kingdom) in 100 ml of dry CH3CN, 6.45 g of NBS are added in 4 equal portions over a period of 1 h at 0-50C under argon. The cooling bath is removed and stirring is continued for 3 h. The solvent is evaporated under vacuum, the residue is dissolved in EtOAc and washed with water and brine. The organic phase is dried over Na2SO4 and evaporated. The title compound is a red-dish-yellow oil which is used after drying in the dark for 5 h at RT and under high vacuum in the next step without further purification. ES-MS (M+1 ): = 239; 241 ; HPLC: tR = 5.501 min. Example 1.4 1 -(2-Methoxy-pyridin-3-yl)-3-methyl-8-(6-methylamino-pyridin-3-yl)-1 ,3-dihydro- imidazo[4,5-c]quinolin-2-one

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, 183610-70-0, 2-Amino-3-(trifluoromethyl)pyridine.

Reference:
Patent; NOVARTIS AG; FURET, Pascal; IMBACH, Patricia; MAH, Robert; STAUFFER, Frederic; WO2010/139747; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 552331-00-7, 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. 552331-00-7, name is 4-Iodopyridin-2-amine. A new synthetic method of this compound is introduced below.

Reference Example 42; 3-(2-aminopyridin-4-yl)-5-phenyl-1,3-oxazolidin-2-oneTo a solution of 4-iodopyridin-2-amine (2.0 g, 9.09 mmol), 5-phenyl-1,3-oxazolidin-2-one (1.7 g, 10.5 mmol) obtained in Reference Example 41 and potassium carbonate (2.5 g, 18.2 mmol) in 1,4-dioxane (30 mL) were added copper iodide (173 mg, 909 mumol) and N,N’-dimethylethylenediamine (80 mg, 909 mumol) at room temperature, and the mixture was heated under reflux for 16 hr under an argon stream. The solid was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate) to give the title compound (1.78 g, yield 77%) as crystals.melting point 155-156 C. (ethyl acetate-hexane)1H-NMR (CDCl3) delta: 3.90 (1H, dd, J=9.0, 7.5 Hz), 4.35 (1H, t, J=9.0 Hz), 4.49 (2H, br s), 5.64 (1H, t, J=7.5 Hz), 6.67 (1H, dd, J=6.0, 2.1 Hz), 6.93 (1H, d, J=2.1 Hz), 7.34-7.50 (5H, m), 8.00 (1H, d, J=6.0 Hz).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,552331-00-7, 4-Iodopyridin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; Takeda Pharmaceutical Company Limited; US2011/39893; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 917023-06-4, 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. 917023-06-4, name is Methyl 2-(5-bromopyridin-2-yl)acetate. A new synthetic method of this compound is introduced below.

A single-necked round-bottomed flask was charged with Compound 2 (1.80g, 7.82mmol), 3-fluorobenzylamine (2.94g, 23.5mmol), and anhydrous anisole 05g). The reaction was stirred at 150C until reaction was complete LCMS (~23h) and then allowed to cool to near RT. Crystals of the desired product, Compound 3, formed during the cooling process and were collected by filtration and washed with toluene. Compound 3 was obtained as colorless crystalline solid (1.59g, 63% yield) and characterized by 1H NMR (400MHz, DMSO-d6): 3 ,69 (s, 2H), 4,30 (d, 2H), 7.0-7.15 (m, 3H), 7.3-7.4 (m, 2H), 7.99 (dd, 1H), 8.61 (fine d, 1H), 8.66 (br t, 1H),

At the same time, in my other blogs, there are other synthetic methods of this type of compound,917023-06-4, Methyl 2-(5-bromopyridin-2-yl)acetate, and friends who are interested can also refer to it.

Reference:
Patent; ATHENEX, INC.; SMOLINSKI, Michael P.; NASIEF ABDEL-SAYED, Nader N.; HANGAUER, JR., David G.; (197 pag.)WO2018/31988; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 76006-08-1, 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. 76006-08-1, name is 5-Chloro-1H-pyrazolo[3,4-c]pyridine, molecular formula is C6H4ClN3, 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 5-chloro-1H-pyrazolo[3,4-c]pyridine (15 g, 1 equiv) in DMF (150 mL) was added iodine (37.2 g, 1.5 equiv) and potassium hydroxide (13.7 g, 2.5 equiv) at 0 C. The reaction mixture was stirred at room temperature for 12 h and then diluted with 10% aqueous sodium thiosulfate (250 mL) and extracted with EtOAc. The combined organic extracts were washed with brine and then dried. The obtained solid (15 g) was slurried with MTBE, filtered and dried.

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 76006-08-1, 5-Chloro-1H-pyrazolo[3,4-c]pyridine.

Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason, Allan; PHADKE, Avinash, S.; DESHPANDE, Milind; AGARWAK, Atul; CHEN, Dawei; GADHACHANDA, Venkat, Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; (905 pag.)WO2017/35353; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 24517-64-4, Adding some certain compound to certain chemical reactions, such as: 24517-64-4, name is 2-Amino-3-cyanopyridine,molecular formula is C6H5N3, 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 24517-64-4.

8.1 Compound 9: 2-Aminonicotinonitrile 8 (100 g, 0.839 mol) was dissolved in HOAc (800 mL) . To the solution was added Na2C03 (88.97 g, 0.839 mol). Then, Br2 (46.4 mL, 0.923 mol) was added dropwise. The reaction mixture was stirred at room temperature for 50 min. To the mixture was added water (600 mL) . The mixture was cooled to about 5C. The precipitate thus formed was collected by filtration and dried to give compound 9 (207 g, 96%) .

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. 24517-64-4, 2-Amino-3-cyanopyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; ABUDUSAIMI, Mamuti; YE, Fangguo; SUN, Jiangqin; MIYAMOTO, Hisashi; CHENG, Jay-Fei; OKA, Daisuke; WO2013/29548; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1121-60-4, 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. 1121-60-4, name is Picolinaldehyde. A new synthetic method of this compound is introduced below.

General procedure: To a mixture of 1,2-phenylenediamines (1.0 mmol) andaldehydes (1.1 mmol) in ethanol, 25 mol % of Ag2CO3/Celite (3 mL) was added. The resulting mixture was stirredat 70 C for 3 h. After this time, the reaction mixture wasdiluted with ethanol (50 mL) and the catalyst was separatedby filtration. Water was then added to the organic layer, andthe products were filtered and washed with water. All of theproducts are known compounds and characterized easily bycomparison with melting point, IR, [1-6] H NMR spectraldata reported in literature.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1121-60-4, Picolinaldehyde, and friends who are interested can also refer to it.

Reference:
Article; Soleimani, Ebrahim; Khodaei, Mohammad Mehdi; Yazdani, Hossein; Saei, Parisa; Zavar Reza, Javad; Journal of the Iranian Chemical Society; vol. 12; 7; (2015); p. 1281 – 1285;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem