Category: pyridine-derivatives

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

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

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

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

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

Reference of 1186637-43-3, Adding some certain compound to certain chemical reactions, such as: 1186637-43-3, name is 3-Bromo-6-methoxypicolinonitrile,molecular formula is C7H5BrN2O, 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 1186637-43-3.

To a solution of 3-bromo-6-methoxypicolinonitrile (1eq) in EtOH was added NaOH (3eq). The reaction was warmed to 100 C for 12 h, and then cooled and acidified with 2M HCl until the pH ~4-5. The reaction was concentrated to remove the EtOH, and then diluted with EtOAc and water. The layers were separated. The organic layer was washed with brine, dried (MgSO4) and concentrated in vacuo to give the title compound which was used without further purification. ESI-MS (m/z): 231.99 [M+1]+.

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. 1186637-43-3, 3-Bromo-6-methoxypicolinonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; EOLAS THERAPEUTICS, INC.; KAMENECKA, Theodore, M.; HOLENZ, Joerg; WESOLOWSKI, Steven; HE, Yuanjun; BUeRLI, Roland; (201 pag.)WO2017/139603; (2017); 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. 944317-27-5, name is 6-Bromo-3-chloro-2-methylpyridine, the common compound, a new synthetic route is introduced below. Quality Control of 6-Bromo-3-chloro-2-methylpyridine

: 2-(tributylstannyl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole (2.69 g, 6.78 mmol), 6-bromo-3-chloro-2-methyl-pyridine (700.00 mg, 3.39 mmol), lithium chloride (287.43 mg, 6.78 mmol) and tetrakis(triphenylphosphine)palladium (391.77 mg, 339.00 mumol) were added to dioxane (30 mL). The reaction mixture was charged with nitrogen three times, then heated to 100-110 C and stirred for 12 h. The mixture was quenched by pouring into water (50 mL) and extracted with ethyl acetate (50 mL*3). The combined organic phases were washed with brine (100 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatograph (eluent: petroleum ether/ethyl acetate=10/1-5/1) to give 2-(5-chloro-6-methylpyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b] pyrazole (600.00 mg, yield: 67.19%). 1H NMR (400MHz, CHLOROFORM-d) 7.65(q, J = 8.4 Hz, 2H), 6.59(s, 1H), 4.22(t, J = 7.2 Hz, 2H), 2.95(t, J = 7.3 Hz, 2H), 2.71-2.59(m, 5H).

The synthetic route of 944317-27-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Genfleet Therapeutics (Shanghai) Inc.; Medshine Discovery Inc.; SUN, Fei; WU, Lifang; DING, Charles Z.; HU, Guoping; LI, Jian; CHEN, Shuhui; LU, Jianyu; (45 pag.)EP3470409; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 19346-44-2, name is 2-Fluoro-3-nitro-5-methylpyridine, molecular formula is C6H5FN2O2, 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. Computed Properties of C6H5FN2O2

To a stirred solution of 2-fluoro-5-methyl-3-nitropyridine 4a (3.0 g, 19.22 mmol) in carbon tetrachloride (80 mL) were added azodiisobutyronitrile (316 mg, 1.90 mmol) and N-bromosuccinimide (3.76 g, 21.14 mmol). The reaction mixture was heated at reflux for 48 h under an argon atmosphere and then the contents were cooled to room temperature. The insoluble solid was removed by filtration, the filtrate was diluted with dichloromethane (50 mL) and washed with saturated aqueous sodium bicarbonate (30 mL×4) and brine (20 mL×2), dried over anhydrous magnesiumsulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (petroleum ether/dichloromethane/ ethyl acetate = 15:1:1) to give the title compound 5a (1.8 g, 35.5%). White solid; mp 73-75 C; 1H NMR (400 MHz, CDCl3) delta (ppm): 8.56 (d, J = 8.4 Hz, 1H), 8.50 (s, 1H), 4.52 (s, 2H)

With the rapid development of chemical substances, we look forward to future research findings about 19346-44-2.

Reference:
Article; Zhao, Hailong; Ji, Ming; Cui, Guonan; Zhou, Jie; Lai, Fangfang; Chen, Xiaoguang; Xu, Bailing; Bioorganic and Medicinal Chemistry; vol. 25; 15; (2017); p. 4045 – 4054;,
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 2897-43-0, name is 2,6-Dichloro-3-nitropyridin-4-amine. This compound has unique chemical properties. The synthetic route is as follows. category: pyridine-derivatives

To a solution of intermediate 12 (37.00 g, 177.88 mmol) in HCl (60 mL) and (EtOH/H2O solution (400 mL, 1:1, v/v) was added Iron powder (30.00 g, 537.20 mmol). The reaction mixture was stirred at 100 C for 3 hours. The reaction mixture was concentrated and diluted with water. The suspended solution was basified by aqueous NaHCO3 solution until pH=9. The precipitate was filtered and diluted in a mixture of EtOAc/MeOH (8:1, v/v). The remaining solid was filtered and the filtrate was concentrated under vacuum to afford a first batch of intermediate 13.

With the rapid development of chemical substances, we look forward to future research findings about 2897-43-0.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; PILATTE, Isabelle, Noelle, Constance; QUEROLLE, Olivier, Alexis, Georges; ANGIBAUD, Patrick, Rene; BERTHELOT, Didier, Jean-Claude; COUPA, Sophie; DEMESTRE, Christophe, Gabriel, Marcel; MEERPOEL, Lieven; MERCEY, Guillaume, Jean, Maurice; MEVELLEC, Laurence, Anne; MEYER, Christophe; PASQUIER, Elisabeth, Therese, Jeanne; PONCELET, Virginie, Sophie; (104 pag.)WO2017/216293; (2017); 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. 6318-51-0, name is (4-Chlorophenyl)(pyridin-2-yl)methanone, the common compound, a new synthetic route is introduced below. Formula: C12H8ClNO

A 20 mL Schlenk tube was charged with 33 mg of catalyst 1a, 0.23 g of (2-pyridyl) methanone-N-oxide, 5 mL of formic acid / triethylamine mixture 1). The tube was sealed and replaced with nitrogen for 3 times. The reaction was carried out at 40 C for 24 hours. After the reaction was completed, water was added and the mixture was extracted with ethyl acetate for 3 times. The mixture was concentrated to dryness and purified to give 0.22 g of a white solid with a yield of 95% The product (S) – (4-chlorophenyl) (2-pyridyl) methanol-N-oxide was determined by HPLCEnantiomeric excess ee was 92%.

The synthetic route of 6318-51-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Yichang Renfu Pharmaceutical Co., Ltd.; China Three Gorges University; Fu Yigang; Lv Jinliang; Zhou Haifeng; Wang Baigui; Cao Lu; Zheng Huazhang; Tian Luanyuan; Li Shiqun; Li Lie; Du Wentao; (13 pag.)CN106938995; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem