Pyridine-derivatives

Synthetic Route of 197376-47-9 ,Some common heterocyclic compound, 197376-47-9, molecular formula is C9H10ClNO2, 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.

Reference Example 74 ethyl [6-(methylsulfanyl)pyridin-3-yl]acetate To a solution of ethyl (6-chloropyridin-3-yl)acetate (10.7 g) in N,N-dimethylformamide (100 mL) was added sodium methanethiolate (11.3 g), and the mixture was stirred at room temperature for 23 hr. The reaction mixture was diluted with ethyl acetate, washed successively with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane =5:95 – 50:50, volume ratio) to give the title compound (4.55 g, yield 40%) as a colorless oil. MS:212(MH+). _

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. 197376-47-9, Ethyl 6-Chloropyridine-3-acetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2149550; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 13445-16-4, 3-Bromo-2,6-dimethoxypyridine, 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, Quality Control of 3-Bromo-2,6-dimethoxypyridine, blongs to pyridine-derivatives compound. Quality Control of 3-Bromo-2,6-dimethoxypyridine

Preparation 7 (Z,E)-Ethyl 3-(2,6-dimethoxypyridin-3-yl)-3-ethoxyacrylate Bis(tri-t-butylphosphine)palladium (47 mg, 0.092 mmol)) and lithium chloride (292 mg, 0.27 mmol) were added to a flask equipped with reflux condenser, and the apparatus was evacuated under vacuum and refilled with N2 several times. To this flask was added via cannula a degassed solution of anhydrous 1,4-dioxane (8 mL) under N2, followed by 3-bromo-2,6-dimethoxypyridine (500 mg, 2.29 mmol), N,N-dicyclohexylmethylamine (540 uL, 2.52 mmol) and ethyl 3-ethoxyacrylate (1.0 mL, 6.88 mmol), and the resulting orange solution was heated to 110 C. After 20 hours, the reaction mixture was cooled to room temperature, quenched with water and diluted with EtOAc. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic extracts were washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by chromatography on silica eluting with 0-50% EtOAc/heptane to yield the title compound (604 mg, 94%) as an amber oil. 1H NMR showed the product to be composed of a 2.5:1 mixture of E/Z isomers.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,13445-16-4, 3-Bromo-2,6-dimethoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; Carpino, Philip A.; Conn, Edward L.; Dow, Robert L.; Dowling, Matthew S.; Hepworth, David; Kung, Daniel Wei-Shung; Orr, Suvi; Rocke, Benjamin N.; Ruggeri, Roger B.; Sammons, Matthew F.; Warmus, Joseph S.; Zhang, Yan; US2013/123230; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1214377-45-3, 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. 1214377-45-3, name is 2-Chloro-6-(difluoromethoxy)pyridine, molecular formula is C6H4ClF2NO, 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.

At room temperature, 2-chloro-6- (difluoromethoxy) pyridine (40.00g, 222.78mmol),Trifluoroacetic anhydride (120ml), fuming nitric acid (16.00g, 229.46mmol) was added dropwise at 0 C, and the reaction was performed at 0-10 C for 2h.Add ice water (1000 ml), extract with methyl tertiary ether (300 ml x 3), combine the organic phases, concentrate,Column chromatography gave 25.00 g of a pale yellow solid with a yield of 50%.

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 1214377-45-3, 2-Chloro-6-(difluoromethoxy)pyridine.

Reference:
Patent; Jiangsu Weikaier Pharmaceutical Technology Co., Ltd.; Gong Yanchun; Meng Lei; Guo Qirun; Liu Yongqiang; (65 pag.)CN110642838; (2020); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 851607-27-7, 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 851607-27-7 as follows.

[1037] To a stirred mixture of compound 3 (4 g, 18.1 mmol), compound 4 (4.52 g 21.72 mmol), and K2CO3 (5 g, 36.2 mmol) in DME/H2O (48 mL, v/v=5/1) was added Pd(dppf)Cl2 (668 mg, 0.91 mmol) under N2 protection. The reaction mixture was degassed with nitrogen again and refluxed overnight. The mixture was concentrated, diluted with H2O and extracted with EtOAc. The combined organic layer was washed with brine, dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was purified by column chromatography (PE/EA=2/1) to give compound 5 (2.8 g, 69% yield) as a pale yellow solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,851607-27-7, its application will become more common.

Reference:
Patent; Buckman, Brad Owen; Nicholas, John Beamond; Ramphal, Johnnie Y.; Emayan, Kumaraswamy; Seiwert, Scott D.; US2014/94456; (2014); 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. 54718-39-7, name is 2,5,6-Trichloronicotinic acid. A new synthetic method of this compound is introduced below., SDS of cas: 54718-39-7

1,1 ?-Carbonyldiimidazole (40 g, 247 mmol) was added in portions to 2,5,6- trichloronicotinic acid (50.7 g, 224 mmol, Combi-Blocks, San Diego, Calif.) in THF (400 mE), allowing gas evolution to cease between addition. The resulting mixture was stirred for 5 mm and then was degassed with house vacuum and flushed with nitrogen. The resulting mixture was heated to 50 C. for 60 mm, then diluted with toluene (100 mE) and concentrated to half the initial volume. The resulting mixture was cooled to 0 C. and ammonium hydroxide (60 mE, 437 mmol) was added slowly via syringe. The reaction was stirred for 10 mm at it, diluted with EtOAc (200 mE) and washed with water (3×100 mE). The organic layer was dried over anhydrous Na2504 and concentrated in vacuo. The residue was suspended in 9:1 heptane/EtOAc (300 mE) and filtered. The filtered solids were collected and the remaining mother liquor was partially evaporated to half the initial volume, cooled to 0 C., and filtered. The two crops of filtered solids were combined to provide 2,5,6-trichloroni- cotinamide.

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, 54718-39-7, 2,5,6-Trichloronicotinic acid.

Reference:
Patent; Amgen Inc.; LANMAN, Brian Alan; BOOKER, Shon; GOODMAN, Clifford; REED, Anthony B.; LOW, Jonathan D.; WANG, Hui-Ling; CHEN, Ning; MINATTI, Ana Elena; WURZ, Ryan; CEE, Victor J.; (88 pag.)US2019/77801; (2019); 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. 83393-46-8, name is 1-(1H-Pyrrolo[2,3-b]pyridin-3-yl)ethanone. A new synthetic method of this compound is introduced below., Formula: C9H8N2O

General procedure: To a 20 ml or 40 ml viale quipped with a stir bar was added photocatalyst, nitrogen nucleophile, iodomesitylene dicarboxylate, copper salt, and ligand. Dioxane was added followed by addition of the base. The solution was sonicated for 1-3 min until it became homogeneous. Next, the solution was degassed by sparging with nitrogen for 5-10 min before sealing with Parafilm. The reaction was stirred and irradiated using two 34-W blue LED lamps (3 cm away, with cooling fan to keep the reaction at room temperature) for 1 h. The reaction mixture was removed from the light, cooled to ambient temperature, diluted with water (15 ml) and ethyl acetate (25 ml), and the aqueous layer was extracted with ethyl acetate (3 × 25 ml). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography on silica gel to afford the desired decarboxylative C-N coupling product. For aniline substrates, a solution of these nitrogen nucleophiles in dioxane was used; additionally, if the iodomesitylene dicarboxylate is a liquid, its solution in dioxane was used.

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, 83393-46-8, 1-(1H-Pyrrolo[2,3-b]pyridin-3-yl)ethanone.

Reference:
Article; Liang, Yufan; Zhang, Xiaheng; MacMillan, David W. C.; Nature; vol. 559; 7712; (2018); p. 83 – 88;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1401624-81-4, 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 1401624-81-4 as follows.

A solution of 2,6-dlbromo-[1 ,2,4]trlazolo[i,5-a]pyrldlne (2.7 g, 9.7 mmol), triethylamlne (2.94 g, 29.1 mmol), and N-methylpiperazlne (1.94 g, 19.4 mmol) in toluene was refluxed overnight. The solvent was removed under vacuum, and the residue was purified by HPFC (PE: EA -1 : 1) to yield PZ972-3 (1.82 g, 63%). LC-MS: 296.1, 298.1 (M+l).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1401624-81-4, its application will become more common.

Reference:
Patent; PROZYMEX A/S; PEDERSEN, John; LAURITZEN, Conni; WO2012/130299; (2012); A1;,
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. 124870-33-3, name is Methyl 2-(3-cyanopyridin-4-yl)acetate, the common compound, a new synthetic route is introduced below. HPLC of Formula: C9H8N2O2

1.58g of (3-cyano-pyridine-4-yl) -acetic acid methyl ester was dissolved in 18 mL of ethanol and slowly added with 682mg of sodium borohydride at-0 C and stirred for about 2 hours. The above mixture was added with 3 mL of saturated solution of ammonium chloride, diluted with 200 mL ethylacetate. Then, the organic solvent layer was washed with water, and saturated solution of sodium chloride, dried with anhydrous sodium sulfate and filtered. The filtrate was concentreated under reduced pressure and a silica gel column chromatography was performed on the resulting residue by using a mixed eluant of methylene chloride and methanol, wherein methylene chloride and methanol are mixed in 50: 1 volume ratio, and 1.02g (74%) of 4- (2-hydroxy-ethyl)-nicotinonitrile was obtained in colorless oil. 1H NMR (300 MHz, CDCI3) 8 8. 82 (s, 1H), 8.69 (d, 1H, J=5. 4Hz), 7.39 (d, 1H, J=5. 4Hz), 3.99 (t, 2H, J=6. 3Hz), 3.10 (t, 2H, J=6. 3Hz).

The synthetic route of 124870-33-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SK CHEMICALS, CO., LTD.; WO2005/63768; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 121643-44-5, Adding some certain compound to certain chemical reactions, such as: 121643-44-5, name is 2-Methoxy-3-(trifluoromethyl)pyridine,molecular formula is C7H6F3NO, 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 121643-44-5.

2-Methoxy-3-trifluoromethyl-pyridine (2.7 g, 14.79 mmol) and 1 ,3-dibromo-5,5- dimethylhydantoin (5.28g, 18.48 mmol) were placed in a round-bottom flask. To this mixture was slowly added 40ml TFA. The mixture was stirred overnight at ambient temperature (16h). After completion of the reaction, TFA solvent was evaporated in vacuo and the resulting residue was neutralized to pH6-7 by the addition of saturated NaHC03. The aqueous layer was extracted with DCM two times and the combined extract was washed with brine, dried over magnesium sulfate and concentrated in vacuo to give a mixture of oil and white solid. The residue was redissolved into 20% Ethylacetate/Heptane (50ml) and the insoluble white solid was filtered off. The filtrate was concentrated and then purified by Flash- chromatography on silica gel (EtOAc/Heptane 5/95) to give 5-Bromo-2-methoxy-3- trifluoromethyl-pyridine as a colorless liquid (2.08 g, 52% yield).1 H-NMR (400 MHz, DMSO-d6, 298 K): ? ppm 4.03 (s, 3H) 7.95 (d, 1 H) 8.4 (d, 1 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. 121643-44-5, 2-Methoxy-3-(trifluoromethyl)pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; FURET, Pascal; HEBACH, Christina; HOeGENAUER, Klemens; HOLLINGWORTH, Gregory; LEWIS, Ian; SMITH, Alexander, Baxter; SOLDERMANN, Nicolas; STAUFFER, Frederic; WOLF, Romain; ZECRI, Frederic; WO2013/57711; (2013); 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. 19346-43-1, name is 2-Fluoro-3-nitro-4-picoline. A new synthetic method of this compound is introduced below., Recommanded Product: 19346-43-1

26. Preparation of 3-Amino-2-fluoro-4-methylpyridine To a solution of 10.1 g (65 mmol) of 2-fluoro-4-methyl-3-nitropyridine in 200 mL of ethyl acetate was added 25 g (0.40 mol) of acetic acid and 0.8 g of 5 percent palladium on carbon catalyst. This mixture was shaken under 50 psig (pounds per square inch gauge) (2400 kiloPascals) pressure of hydrogen for 18 hours, was filtered, and was concentrated by evaporation under reduced pressure to obtain an oil. This oil was partitioned between dilute aqueous sodium bicarbonate and ether. The organic phase was recovered, dried over magnesium sulfate, and filtered. The filtrate was concentrated by evaporation under reduced pressure and the residue was purified by column chromatography to obtain 7.2 g (88 percent of theory) of the title compound as a colorless solid melting at 63-64 C. Nuclear Magnetic Resonance Spectrum (200 MHz (megaHertz), CDCl3): 1 H: 7.4 (d, 1H, J=5.0); 6.8 (d, 1H, J=5.0); 3.7 (br, 2H); 2.1 (s, 3H); 13 C: 152.6 (d, J=229); 134.1 (d, J=8.6); 133.8 (d, J=14.5); 128.1 (d, J=27.1); 123.3, 16.4 (d, J=4.1).

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, 19346-43-1, 2-Fluoro-3-nitro-4-picoline.

Reference:
Patent; DowElanco; US5494887; (1996); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem