Day: April 11, 2022

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. 1149-24-2, name is Diethyl 2,6-dimethylpyridine-3,5-dicarboxylate, molecular formula is C13H17NO4, 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. Recommanded Product: Diethyl 2,6-dimethylpyridine-3,5-dicarboxylate

General procedure: To a mixture of ethyl acetoacetate or methyl acetoacetate (1 eqv), formaldehyde (1.1 eqv) and NH4OAc (1.5 eqv) in acetic acid (3 mL) was added FeWO4 (20 mol%) at room temperature and the mixture was heated at 80 C for 2 h (monitoring by TLC) to give poly-substituted pyridine (3), to this solution isatin (1 eqv) was added and heating continued at same temperature for 3 h (monitoring by TLC). After that the reaction mixture was cooled to room temperature neutralized with sodium bicarbonate and extracted with EtOAc (2 × 10 mL). The organic layers were washed with brine, dried using sodium sulphate .Evaporation of the solvent gave the crude product which was purified by silica gel column chromatography. Elution of the column with petroleum ether-EtOAc gave the desired product.

With the rapid development of chemical substances, we look forward to future research findings about 1149-24-2.

Reference:
Article; Paplal, Banoth; Nagaraju, Sakkani; Sathish, Kota; Kashinath, Dhurke; Catalysis Communications; vol. 103; (2018); p. 110 – 115;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 875781-18-3, 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. 875781-18-3, name is 5-Bromo-3-iodo-1H-pyrazolo[3,4-b]pyridine. A new synthetic method of this compound is introduced below.

5-bromo-3-iodo-1H-pyrazolo[3,4-b]pyridine ((II), 10.44 g, 32.2 mmol) was combined with DMF, MeOH and triethylamine (75 mL each). The vessel was evacuated and flushed with argon (4x). XantPhos (1.12 g, 1.93 mmol) and Pd(OAc)2 (217 mg, 0.97 mmol) were added and carbon monoxide (generated from formic acid and sulfuric acid) was bubbled through the solution while heating to 60 C. The mixture was stirred under an atmosphere of carbon monoxide (balloon) for 8 h. Every 1.5 h carbon monoxide was bubbled through the solution for 5 minutes. The mixture was concentrated under reduced pressure and the residue was triturated with 2N HCl. The solids were heated at 95 C in about 100 mL 1N NaOH overnight. After cooling to RT, the mixture was acidified with conc. HCl and the precipitate collected by suction filtration and washed with water. The solids were dried in an oven at 110 C to constant mass. The solids were sonicated in 100 mL of toluene for 5 minutes and stirred for 30 minutes. The product was filtered, washed with an additional 20 mL of toluene and dried at 110 C. Yield: 7.92 g HPLC purity: > 99 %, 1H NMR (200 MHz, DMSO) delta 8.64 (d, J = 7.9 Hz, 2H), 5.69 (bs, 1H); 13C NMR (50 MHz, DMSO) delta 163.27, 150.97, 149.67, 136.69, 132.65, 115.73, 113.6; [M-H]- = 239.9 / 241.9.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,875781-18-3, 5-Bromo-3-iodo-1H-pyrazolo[3,4-b]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; HEPAREGENIX GMBH; PRAEFKE, Bent; KLOeVEKORN, Philip; SELIG, Roland; ALBRECHT, Wolfgang; LAUFER, Stefan; (157 pag.)WO2019/149738; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 936011-17-5, 5-Bromo-2-methoxyisonicotinaldehyde, 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 5-Bromo-2-methoxyisonicotinaldehyde, blongs to pyridine-derivatives compound. Quality Control of 5-Bromo-2-methoxyisonicotinaldehyde

The solution of 5-bromo-2-methoxy-pyridine-4-carbaldehyde (CAS: 936011-17-5, Vendor: Bide, 25.00 g, 115.72 mmol) and ammonium acetate (4.46 g, 57.86 mmol) in nitroethane (150 mL) was stirred at 100 C for 16 hrs. After being cooled down, the mixture was concentrated and purified by flash column (PE/EA = 10/1) to give compound 70a (23.00 g) as a green solid. MS: calc?d 273 (MH+), measured 273 (MH+).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,936011-17-5, 5-Bromo-2-methoxyisonicotinaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; DEY, Fabian; KOU, Buyu; LIU, Haixia; SHEN, Hong; WANG, Xiaoqing; ZHANG, Weixing; ZHANG, Zhisen; ZHANG, Zhiwei; ZHU, Wei; (203 pag.)WO2019/238616; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 72587-18-9, 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. 72587-18-9, name is 2-Chloro-5-(trifluoromethyl)pyridin-3-amine. A new synthetic method of this compound is introduced below.

1-Trimethylsilyl-2-(2-ethylthio-4-trifluoromethylphenyl)ethyne (794 mg), 3-amino-2-chloro-5-trifluoromethylpyridine (650 mg, 1.1 Eq), triethylamine (1 mL), diphenylphosphino ferrocene dichloropalladium (141 mg), copper iodide (33 mg), DMF (5 mL) and a 1 M THF (tetrahydrofuran) solution (4 mL) of tetrabutylammonium fluoride were mixed, and the mixture was heated at reflux under argon for 4 hours. The reaction mixture was concentrated and the resulting residue was subjected to column chromatography to give the desired compound, i.e., 2-(2-ethylthio-4-trifluoromethylphenyl)ethynyl-5-trifluoromethylpyridin-3-amine (0.54 g). The obtained compound was dissolved in DMF (3 mL), potassium t-butoxide (672 mg, 3 Eq) was added to the solution, and the mixture was heated at 100 C. with stirring for 3 hours. After the reaction mixture was allowed to cool down to room temperature, silica gel was added and the mixture was concentrated. The residue was subjected to column chromatography to give 2-(2-ethylthio-4-trifluoromethylphenyl)-6-trifluoromethyl-1H-pyrrolo[3,2-b]pyridine.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,72587-18-9, 2-Chloro-5-(trifluoromethyl)pyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; Nihon Nohyaku Co., Ltd.; Yonemura, Ikki; Sano, Yusuke; Suwa, Akiyuki; Fujie, Shunpei; US2018/352811; (2018); 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. 39903-01-0, name is 2-Amino-5-bromo-3-pyridinol. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of 2-Amino-5-bromo-3-pyridinol

To a mixture of 2-amino-5-bromopyridin-3-ol (5.00 g, 23.5 mmol, CAS 39903-01- 0) in DME (50.0 mL) was added NaOH (3.00 g, 75.0 mmol) in H20 (30.0 mL) dropwise at 10 ~ 20 C. The reaction mixture was degassed under vacuum and chloro(difluoro)m ethane (15.0 psi) was passed through the reaction mixture at 10 ~ 20 C and the mixture was stirred for 16 h. The reaction mixture poured into H20 (100 mL), then extracted with ethyl acetate (50.0 mL x 4). The combined organic layers were washed with brine (100 mL), dried over Na2S04, and concentrated under reduce pressure to get a residue. The residue was purified by column chromatography (Si02, petroleum ether/ethyl acetate = 1/0 to 0/1) to give 5- bromo-3-(difluoromethoxy)pyridin-2-amine (1.70 g, 6.20 mmol, 26% yield) as a yellow solid. LC-MS (ESI+) m/z: 238.7 (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, 39903-01-0, 2-Amino-5-bromo-3-pyridinol.

Reference:
Patent; RELAY THERAPEUTICS, INC.; D.E. SHAW RESEARCH, LLC; TAYLOR, Alexander, M.; LESCARBEAU, Andre; KELLEY, Elizabeth, H.; SHORTSLEEVES, Kelley, C.; WALTERS, W., Patrick; MURCKO, Mark, Andrew; MCLEAN, Thomas, H.; GUNAYDIN, Hakan; GIORDANETTO, Fabrizio; THERRIEN, Eric; (607 pag.)WO2019/183367; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 19346-43-1 ,Some common heterocyclic compound, 19346-43-1, molecular formula is C6H5FN2O2, 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.

2.52 g (0.015 mol) of 2-hydrazine-4-methyl-3-nitropyridine was added to 40 cm3 of n-propanol, 5 cm3 of water, 1 g of sodium bicarbonate and 2.34 g (0.015 mol of 2-fluoro-4-methyl-3-nitro-pyridine. The mixture was heated for 30 min under reflux on a water bath. The mixture changed its color to purple. Then it was evaporated to dryness under reduced pressure and the dry residue was added to 150 cm3 of water, acidified with dilute hydrochloric acid and allowed to stand at room temperature for 12 h. Then the reaction product was filtered and recrystallized with activated carbon. An insoluble product in a form of red-brown needle-shaped crystals was filtered off, dried and re-crystallized twice from ethanol. It was sparingly soluble in water and organic solvents, soluble in glacial acetic acid. The melting point of MNHP was determined giving the value 255 C. More details (e.g. the yield and the chemical analysis) of the synthesis can be found in our publications [16,19].

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. 19346-43-1, 2-Fluoro-3-nitro-4-picoline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kucharska; Bryndal; Hanuza; Lis; Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy; vol. 127; (2014); p. 303 – 309;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 947249-27-6, 2-Bromo-3-(difluoromethoxy)pyridine, 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, 947249-27-6, blongs to pyridine-derivatives compound. Recommanded Product: 947249-27-6

To a steel bomb were charged with 2-methoxyethanol (20 ml), 2-bromo-3-(difluoromethoxy)pyridine (1.95 g, 8.7 mmol), conc. aqueous NH4OH (28-30%, 5 ml, 79 mmol) and Cu2O (0.25 g, 1.7 mmol). The reaction mixture was heated at 100 C. for 23 h, then cooled to 0 C., and partitioned between mixture of EtOAc/aq. 3 N NaOH/H2O (40 ml/10 ml/30 ml). The organic phase layer was collected, washed with saturated aqueous NaHCO3 solution (30 ml), brine (40 ml), dried (Na2SO4), and concentrated to produce 1.12 g of 3-(difluoromethoxy)pyridin-2-amine which was carried forward without further purification: LCMS (m/z, MH+): 161.0, tR=0.31 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,947249-27-6, its application will become more common.

Reference:
Patent; Huang, Zilin; Jin, Jeff; Machajewski, Timothy; Antonios-McCrea, William R.; McKenna, Maureen; Poon, Daniel; Renhowe, Paul A.; Sendzik, Martin; Shafer, Cynthia; Smith, Aaron; Xu, Yongjin; Zhang, Qiong; Chen, Zheng; US2013/210818; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 20970-75-6, 2-Cyano-3-methylpyridine, 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, 20970-75-6, blongs to pyridine-derivatives compound. Recommanded Product: 2-Cyano-3-methylpyridine

Example 8rac-N-(((2S,3R)-3 -Methyl-i -(2-methyl-S -phenylthiazole-4-carbonyl)piperidin-2- ylmethyliuinoline-8-carboxamide3 -MethylpicolinamideLN_I,NH20A mixture of 3-methylpicolinonitrile (2.36 g, 20 mmol) and conc. sulfuric acid (12.5mL) was stirred at 80C for 25 mm. The solution was cooled to r.t., poured into water (80mL), followed by addition of sat. Na2CO3 (aq.) until pH 7. The resulting mixture was extracted with DCM (3x) and the combined organic layer was dried over Mg504 and concentrated in vacuo to provide 3-methylpicolinamide as a white solid (2.65 g, 97%). ?H74NMR (CDC13, 400 MHz) oe 8.43 (dd, 1H), 7.93 (brs, 1H), 7.62 (dd, 1H), 7.35 (dd, 1H), 5.44 (brs, 1H), 2.76 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,20970-75-6, its application will become more common.

Reference:
Patent; EOLAS THERAPEUTICS, INC.; KAMENECKA, Theodore; JIANG, Rong; SONG, Xinyi; WO2013/119639; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 960289-03-6, Adding some certain compound to certain chemical reactions, such as: 960289-03-6, name is 2-Bromo-5,6-dihydrothieno[2,3-c]pyridin-7(4H)-one,molecular formula is C7H6BrNOS, 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 960289-03-6.

A solution of tert-butyl (3-(4,4,5,5-tetra methyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)carbamate (416 mg, 1.3 mmol), 2-bromo-5,6-dihydrothieno[2,3-c]pyridin-7(4H)-one (300 mg, 1.3 mmol) and Pd(PPh3)4 (23 mg, 0.02 mmol) in n-BuOH (3 mL) and 2M Na2CO3 (3 mL) was degassed under bubbling nitrogen and the reaction was heated 2 h at 100 C. Upon completion, the reaction was filtered and concentrated under reduced pressure, then partitioned between DCM (10 mL) water (10 mL). The layers were separated and the aqueous layer was extracted with DCM (3×10 mL). The combined organics were dried over Na2SO4 and concentrated. The concentrate was slurried in EtOAc, sonicated and filtered to afford 2-(2-aminopyridin-3-yl)-5,6-dihydrothieno[2,3-c]pyridin-7(4H)-one (281 mg, 88% yield) as a white solid. 1H NMR (300 MHz, MeOH) delta ppm 7.99 (dd, J=5.0, 1.3 Hz, 1H), 7.62 (dd, J=7.5, 1.4 Hz, 1H), 7.25 (s, 1H), 6.76 (dd, J=7.5, 5.1 Hz, 1H), 3.61 (t, J=7.0 Hz, 2H), 2.97 (t, J=7.1 Hz, 2H); MS (EI) m/z=246.3 [M+1]+.

According to the analysis of related databases, 960289-03-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Augeri, David John; Bagdanoff, Jeffrey Thomas; Baugh, Simon David Peter; Carlsen, Marianne; Carson, Kenneth Gordon; Gilleran, John Anthony; He, Wei; Oravecz, Tamas; Salojin, Konstantin; Sung, Leonard; US2012/225857; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 63237-88-7, Pyrazolo[1,5-a]pyridine-2-carboxylic 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, Product Details of 63237-88-7, blongs to pyridine-derivatives compound. Product Details of 63237-88-7

To a stirred solution of compound A (500 mg, 3.08 mmol, 1 eq) in CH2CI2 (15 ml) was added thionyl chloride (0.665 ml, 9.25 mmol, 3 eq) and the mixture was refluxed for 3 h. The mixture was cooled to RT, concentrated in vacuo and the residue was dissolved in CH2CI2 (20 ml). TEA (3 ml, 21.51 mmol, 7 eq) followed by Weinreb amine salt (450 mg, 4.62 mmol, and 1.5 eq) was added to it and the resulting mixture was stirred at 23 C for 16 h. The reaction mixture was diluted with ethyl acetate (150 ml), the combined organic layer was washed with water and brine. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. The crude material was purified by column chromatography to obtain compound B (400 mg, 63 %) as liquid compound. (0425) [0402] FontWeight=”Bold” FontSize=”10″ H NMR (DMSO-d6) delta 8.72-8.70 (d, / = 8 Hz, 1 H), 7.76-7.74 (d, / = 9 Hz, 1 H), (0426) 7.30-7.26 (m, 1 H), 7.02-7.00 (t, / = 7 Hz, 1 H), 3.73 (s, 3 H), 3.37 (s, 3 H); (0427) [0403] LCMS: m/z = 206.0 [M+H], RT = 2.27 minutes; (Program PI, Column v.

The synthetic route of 63237-88-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASANA BIOSCIENCES, LLC; THOMPSON, Scott, K.; PRIESTLEY, Tony; KUNDU, Mrinalkanti; SAHA, Ashis; NATH, Suvadeep; (126 pag.)WO2018/64135; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem