Day: April 20, 2022

Electric Literature of 867279-13-8, 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. 867279-13-8, name is 4-Bromo-2-chloro-5-methylpyridine. A new synthetic method of this compound is introduced below.

To a solution of 4-bromo-2-chloro-5-methylpyridine (0.15 g, 0.73 mmol) in DCM (5 ml) was added 77% mCPBA (0.33 g, 1.45 mmol). The resulting mixture was stirred at rt for 3 days. EtOAc was added followed by 1 : 1 mixture of Na2SO3 and Na2CO3 solutions. The resulting mixture was stirred vigorously for 0.5 hour and the organic phase was separated. The aqueous phase was extracted with EtOAc. The combined organic phases were washed with aq. ‘Na2C03 solution and brine, dried with Na2S04, filtered and evaporated yielding 0.13 g of 4-bromo-2-chloro-5-methylpyridine 1 -oxide. 1H NMR (CDCi3) delta: 8.20-8.23 (m, 1 1 1), 7.66 (s, 1-Iota), 2.31-2.34 (m, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,867279-13-8, 4-Bromo-2-chloro-5-methylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; RICHTER GEDEON NYRT.; ORION CORPORATION; HAIKARAINEN, Anssi; JOUBERT, Muriel; KAROLYI, Benedek; KAeSNAeNEN, Heikki; PASSINIEMI, Mikko; POHJAKALLIO, Antti; SZANTO, Gabor; VAISMAA, Matti; (97 pag.)WO2019/43635; (2019); 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. 884495-00-5, name is 4-Bromo-5-fluoro-2-methoxypyridine, the common compound, a new synthetic route is introduced below. Recommanded Product: 884495-00-5

A solution of 4-bromo-5-fluoro-2-methoxypyridine (1.0 g, 4.8 mmol) in THF (15 mL) was cooled to -78 C and n-butyllithium (2.2 mL, 5.5 mmol, 2.5 M in THF) was added drop-wise. The resulting mixture was stirred at -78 C for 10 min and a solution of ethyl 4-oxocyclohexanecarboxylate (1.2 g, 7.3 mmol) in THF (5 mL) was added drop-wise with stirring. The resulting solution was stirred for 2 h at -78 C, poured into 100 mL of saturated, aq. H4CI and extracted with ethyl acetate (3 x 100 mL). The separated organic layers were combined, dried over Na2S04 and concentrated. The residue obtained was purified on silica gel with ethyl acetate/petroleum ether (0-20%) to give compound 25a. Mass Spectrum (LCMS, ESI pos.): Calcd. For C15H20FNO4: 298.1 [M+H]+; found: 297.9.

The synthetic route of 884495-00-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; HUANG, Hui; LANTER, James C.; MEEGALLA, Sanath K.; PLAYER, Mark R.; (275 pag.)WO2018/81047; (2018); A1;,
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 933721-91-6, name is Imidazo[1,2-a]pyridin-8-ylmethanamine. This compound has unique chemical properties. The synthetic route is as follows. name: Imidazo[1,2-a]pyridin-8-ylmethanamine

A solution of compound 5e (60 mg, 0.15 mmol) and compound 19c (26 mg, 0.18 mmol) in ethanol (0.5 mL) was irradiated at 180 C. in a microwave instrument for two 30 min intervals, then concentrated. The residue was dissolved in methyl sulfoxide and purified by reversed-phase chromatography to furnish the title compound 188 as its trifluoroacetate salt. 1H NMR (methanol-d4): delta 8.66 (d, 1H, J=6.8 Hz), 8.20 (d, 1H, J=2.2 Hz), 8.01 (d, 1H, J=2.2 Hz), 7.46 (d, 1H, J=7.4 Hz), 7.33 (d, 2H, J=8.6 Hz), 7.28 (t, 1H, J=7.0 Hz), 7.15 (d, 2H, J=8.6 Hz), 6.88 (d, 2H, J=8.8 Hz), 6.83 (d, 2H, J=8.8 Hz), 5.15 (s, 2H), 4.96 (s, 2H), 4.88 (s, 2H), 3.78 (s, 3H), 3.75 (s, 3H); HRMS m/z (M+H)+ calcd for C27H27N6O4 499.2094, found 499.2052.

With the rapid development of chemical substances, we look forward to future research findings about 933721-91-6.

Reference:
Patent; Coats, Steven J.; Dyatkin, Alexey B.; He, Wei; Lisko, Joseph; Miskowski, Tamara; Ralbovsky, Janet L.; Schulz, Mark; US2008/269225; (2008); 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. 67310-56-9, name is 1-(5-Hydroxypyridin-2-yl)ethanone. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 67310-56-9

Example 164 2-(4-chloro-3-fluorophenoxy)-iV-[3-(2-{ [6-(l-hydroxyethyl)pyridin-3- yl] oxy }acetamido)bicyclo [ 1.1.1] pentan- 1-yl] acetamide (Compound 263) A mixture of Example 28A (0.1 g, 0.235 mmol), 1 -(5 -hydroxy pyridin-2-yl)ethanone (0.065 g, 0.471 mmol), potassium carbonate (0.065 g, 0.471 mmol) and potassium iodide (2.73 mg, 0.016 mmol) in acetone (2.0 mL) was stirred at 140 C (0-450 W) in a Biotage Initiator microwave reactor for 45 minutes. The suspension was filtered, and the filtrate was concentrated. This residue and NaBH4 (0.089 g, 2.35 mmol) in methanol was stirred at ambient temperature overnight. The reaction mixture was concentrated, and the residue was purified by HPLC (10-85% acetonitrile in 0.1% trifluoroacetic acid/water at 25 rnL/minute on a Phenomenex Luna C18 5 muiotaeta 100 A AXIA column (250 mm chi 21.2 mm)) to give 59 mg of the title compound as a white solid. XH NMR (400 MHz, DMSO-c) delta ppm 8.74 (d, J = 26.6 Hz, 2H), 8.30 (d, J = 2.8 Hz, 1H), 7.81 – 7.60 (m, 2H), 7.47 (t, J = 8.9 Hz, 1H), 7.05 (dd, J = 11.4, 2.8 Hz, 1H), 6.83 (ddd, J = 9.0, 2.9, 1.2 Hz, 1H), 4.85 (q, J = 6.5 Hz, 1H), 4.61 (s, 2H), 4.46 (s, 2H), 2.25 (s, 6H), 1.37 (d, J = 6.5 Hz, 3H). MS (ESI+) m/z 464.0 (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, 67310-56-9, 1-(5-Hydroxypyridin-2-yl)ethanone.

Reference:
Patent; CALICO LIFE SCIENCES; ABBVIE, INC.; SIDRAUSKI, Carmela; PLIUSHCHEV, Marina; FROST, Jennifer, M.; BLACK, Lawrence, A.; XU, Xiangdong; SWEIS, Ramzi, Farath; SHI, Lei; ZHANG, Qinwei, I.; TONG, Yunsong; HUTCHINS, Charles, W.; CHUNG, Seungwon; DART, Michael, J.; (445 pag.)WO2017/193034; (2017); 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.696-42-4, name is 5-Fluoronicotinonitrile, molecular formula is C6H3FN2, molecular weight is 122.0998, as common compound, the synthetic route is as follows.Recommanded Product: 696-42-4

A mixture of 5-fluoropyridine-3-carbonitrile (1.02 g, 7.91 mmol, 1 eq) and 4-isopropyl-1H- pyrazol-5-amine (880.27 mg, 6.33 mmol, 0.8 eq) in xylene (20 mL) was stirred for 30 min at 70 C. Then AlMe3 (2 M, 4.75 mL, 1.2 eq) was added to above mixture in one portion at 70 C under N2 The mixture was stirred at 100 C for 15 h. LC-MS showed 16% of desired MS was detected. The mixture was quenched by MeOH (20 mL), concentrated to yield a residue which was purified by flash silica gel chromatography (ISCO; 12 g SepaFlash Silica Flash Column, Eluent of 0-10% MeOH/DCM ethergradient (at) 30 mL/min) to yield 5-fluoro-N-(4-isopropyl-lH-pyrazol-5- yl)pyridine-3-carboxamidine (600 mg, 1.94 mmol, 24.5% yield, 80% purity) as a yellow solid. MR (400 MHz, CD3OD) delta ppm 8.96 (s, 1H), 8.54 (d, J = 2.6 Hz, 1H), 8.11 (d, J = 9.5 Hz, 1H), 7.34 (s, 1H), 3.06 (m, 1H), 1.25 (d, J = 6.8 Hz, 6H); ES-LCMS m/z 248.1 [M+H].

At the same time, in my other blogs, there are other synthetic methods of this type of compound,696-42-4, 5-Fluoronicotinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; KYN THERAPEUTICS; CASTRO, Alfredo C.; EVANS, Catherine Anne; (632 pag.)WO2018/195397; (2018); A2;,
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 121643-44-5, name is 2-Methoxy-3-(trifluoromethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 2-Methoxy-3-(trifluoromethyl)pyridine

To 2-methoxy-3-(trifluoromethyl)pyridine (20.0 g, 1 13.0 mmol) and 1 ,3-dibromo-5,5-dimethylimidazolidine-2,4-dione (43.6 g, 152.0 mmol) was added TFA (80 ml_) and the resulting mixture stirred at rt for 8h under argon. The TFA was removed in vacuo (50 mbar, 45C) and the residue suspended in tert-butyl methyl ether (200 ml_). The resultingcolourless solid was removed by filtration and washed with tert-butyl methyl ether (50 mL). The filtrate was concentrated in vacuo and suspended in EtOAc (50 mL) The insoluble colourless solid was removed by filtration and washed with EtOAc (50 mL).The filtrate was concentrated in vacuo, diluted with heptane/ tert-butyl methyl ether (5/1 , 20 mL) and the insoluble colourless solid was removed by filtration. The filtrate was purified by column chromatography on silica gel with heptane / EtOAc, 100/0 to 90/10. The crude product was filtered through a plug of NaHC03 (20g) and the filtrate evaporated in vacuo to give a golden oil (27.9 g). The oil was dissolved in heptanes (20 mL) and purified by filtered through a plug of silica gel (80 g), eluting with heptane to give 5-bromo-2-methoxy-3-(trifluoromethyl)pyridine as a colourless oil (22.5g, 74% yield).1H-NMR (400 MHz, DMSO-d6,298 K): delta ppm 4.03 (s, 3H) 7.95 (d, 1 H) 8.4 (d, 1 H).

With the rapid development of chemical substances, we look forward to future research findings about 121643-44-5.

Reference:
Patent; NOVARTIS AG; COOKE, Nigel Graham; FERNANDES GOMES DOS SANTOS, Paulo Antonio; FURET, Pascal; HEBACH, Christina; HOeGENAUER, Klemens; HOLLINGWORTH, Gregory; KALIS, Christoph; LEWIS, Ian; SMITH, Alexander Baxter; SOLDERMANN, Nicolas; STAUFFER, Frederic; STRANG, Ross; STOWASSER, Frank; TUFILLI, Nicola; VON MATT, Anette; WOLF, Romain; ZECRI, Frederic; WO2013/88404; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 165547-79-5 , The common heterocyclic compound, 165547-79-5, name is 4-Chloro-3-nitro-2(1H)-pyridinone, molecular formula is C5H3ClN2O3, 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.

Silver carbonate (9.50 g, 0.60 equiv) and iodomethane (18.0 mL, 5.00 equiv) were slowly added to a solution of chloro nitro pyridone (10.00 g, 56.2 mmol) in benzene (100 mL). After heating for 8 hrs at 50 C. the reaction mixture was cooled to rt, filtered over celite, and concentrated in vacuo. The crude residue was then redissolved in CH2Cl2, washed with water and brine, dried over MgSO4, concentrated in vacuo and chromatographed (SiO2, 100% CH2Cl2) to provide methyl ether product (5.81 g, 55%).

The synthetic route of 165547-79-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Roche Palo Alto LLC; US2010/56535; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 562825-95-0, 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 562825-95-0, name is N-Ethyl-3-nitropyridin-4-amine. This compound has unique chemical properties. The synthetic route is as follows.

Preparation of N4-ethylpyridine-3,4-diamineHN.>. “2Ethyl-(3-nitropyridin-4-yl)amine (8.7g, 52.0mmol) in ethanol (150ml) was hydrogenated for 18 hours in the presence of 10% palladium on carbon. After filtration of the catalyst through celite, the filtrate was concentrated in vacuo to afford the title compound (6.7g, 94%). 1H NMR (400 MHz, DMSO-D6) delta ppm 1.19 (m, 3H), 3.09 (m, 2H), 4.53 (br, 2H),5.21 (br, 1 H), 6.31 (d, J=5.22 Hz, 1 H), 7.57 (d, J=5.36 Hz, 1 H), 7.62 (s, 1 H). MS (ES+) m/e 138 [M+H]+.

According to the analysis of related databases, 562825-95-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2006/63167; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 13210-52-1, 1-(3-Aminopyridin-4-yl)ethanone, 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, Safety of 1-(3-Aminopyridin-4-yl)ethanone, blongs to pyridine-derivatives compound. Safety of 1-(3-Aminopyridin-4-yl)ethanone

To a solution of 1-(3-aminopyridin-4-yl)ethanone (0.9 g, 6.61 mmol) in DMF (10 mL) was added NBS (2.53 g, 14.21 mmol). The reaction mixture was stirred at room temperature for 2 h. The reaction mixture was diluted with ethyl acetate and saturated NaHCO3 solution. The organic layers (extracted two times) were washed with saturated NaHCO3 solution, dried over MgSO4. The filtrate was concentrated in vacuo. The residue was purified by flash chromatography. The product was eluted with 0-20% ethyl acetate in hexane to give the desired product as a white solid (1.55 g, 80%); HPLC: RT=0.88 min (H2O/ACN with 0.05% TFA, Waters Acquity SDS C18, 2.1×50 mm, 1.7-mum particles, gradient=1.8 min, wavelength=220 nm); MS (ES): m/z=292.8, 294.8 [M+H]+; 1H NMR (400 MHz, CDCl3) delta ppm 7.65 (s, 1H), 6.73 (br. s., 2H), 2.62 (s, 3H).

The synthetic route of 13210-52-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bristol-Myers Squibb Company; Fink, Brian E.; Zhao, Yufen; Borzilleri, Robert M.; Zhang, Liping; Kim, Kyoung S.; Kamau, Muthoni G.; Tebben, Andrew J.; (162 pag.)US2016/176871; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 73112-16-0, 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 73112-16-0, name is 2,6-Dibromo-4-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

Sodium tert-butoxide (0.15 g, 1.56 mmol) and l,l’-bis(di-tert- butylphsophino)ferrocene palladium dichloride (0.078 g, 0.12 mmol) were added to a mixture of 2,6-dibromo-4-methyl pyridine (0.301 g, 1.2 mmol) and tert-butyl carbamate (0.141 g, 1.2 mmol) in nitrogen sparged toluene (3 mL). The slurry was evacuated and refilled with nitrogen. After stirring at 60 C for 4 hours, the solution was cooled to 25 C, water (1 mL) was added and then the mixture extracted with ethyl actetate (2 x 50 mL), dried ( a2S04), filtered and concentrated in reduced pressure. The residue was chromatographed on silica gel to afford tert- butyl (6-bromo-4-methylpyridin-2-yl)carbamate as a white solid (0.3 g, 1.05 mmol). ‘H NMR (600 MHz, CDC13) delta 7.7 (s, 1H), 7.13 (s, 1H), 6.95 (s, 1H), 2.29 (s, 3H), 1.49 (s, 9H).

According to the analysis of related databases, 73112-16-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MERCK CANADA INC.; ANTHONY, Neville, J.; ANDRESEN, Brian, M.; NORTHRUP, Alan, B.; CHILDERS, Kaleen, K.; DONOFRIO, Anthony; MILLER, Thomas, A.; LIU, Yuan; MACHACEK, Michelle, R.; WOO, Hyun Chong; SPENCER, Kerrie, B.; ELLIS, John Michael; ALTMAN, Michael, D.; ROMEO, Eric, T.; GUAY, Daniel; GRIMM, Jonathan; LEBRUN, Marie-Eve; ROBICHAUD, Joel, S.; WANG, Liping; DUBOIS, Byron; DENG, Qiaolin; WO2014/176210; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem