Month: April 2022

Electric Literature of 1026796-81-5, 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.1026796-81-5, name is N-(4-Bromopyridin-2-yl)acetamide, molecular formula is C7H7BrN2O, molecular weight is 215.05, as common compound, the synthetic route is as follows.

To a 15 mL vial was added N-(4-bromopyridin-2-yl)acetamide (205.8 mg, 0.957 mmol), (3-fluoro-4-hydroxyphenyl)boronic acid (239 mg, 1.531 mmol), and Na2C03 (1.435 mL, 2.87 mmol) in dioxane (3 mL) under nitrogen to give a colorless solution. l, -bis(diphenylphosphino)ferrocenepalladium(II) di chloride, toluene (39.4 mg, 0.048 mmol) was added under nitrogen. The vial was sealed and heated at 130 C (microwave) for 2 h. The mixture was partitioned between water and EtOAc. The layers were separated. The organic layer was washed with brine, dried Na2S04) and concentrated under reduced pressure to obtain N-(4-(3-fluoro-4- hydroxyphenyl)pyridin-2-yl)acetamide (200 mg, 0.812 mmol, 85% yield) as a tan solid. LCMS (ESI) m/e 247.0 [(M+H)+, calcd C13H12F1N2O2, 247.1]; LC/MS retention time (method A): /R = 1.51 min.

Statistics shows that 1026796-81-5 is playing an increasingly important role. we look forward to future research findings about N-(4-Bromopyridin-2-yl)acetamide.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BRONSON, Joanne J.; CHEN, Ling; DITTA, Jonathan L.; DZIERBA, Carolyn Diane; JALAGAM, Prasada Rao; LUO, Guanglin; MACOR, John E.; MAISHAL, Tarun Kumar; NARA, Susheel Jethanand; RAJAMANI, Ramkumar; SISTLA, Ramesh Kumar; THANGAVEL, Soodamani; (485 pag.)WO2017/59085; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 60289-67-0, 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.60289-67-0, name is 1-(Pyridin-3-yl)propan-1-amine, molecular formula is C8H12N2, molecular weight is 136.19, as common compound, the synthetic route is as follows.

General procedure: To a solution of ethyl 2- chlorothieno[3,2-(/Jpyrimidine-4-carboxylate (100 mg, 0.41 mmol) and DIEA (0.22 mL, 1.23 mmol) in NMP (3 mL) was added (6-methoxypyridin-3-yl)methanamine hydrochloride (commercially obtained from PharmaBlock, Sunnyvale, CA) (97 mg, 0.89 mmol). The reaction mixture was stirred at 130 C for 3 h. The reaction mixture was cooled to room temperature, diluted with ethyl acetate and washed with 25% aqueous NaCl solution, then with brine three times and dried. The solvent was evaporated and the residue was purified by flash chromatography (24g, HP silica, Teledyne Isco) eluting with 2% to 100% solvent A (DCM/MeOH/NH4OH, 100/10/1) in DCM to provide 2-chloro-N-((6-methoxypyridin-3- yl)methyl)thieno[3,2-Patent; CORVUS PHARMACEUTICALS, INC.; LI, Zhihong; FILONOVA, Lubov, Konstantinovna; BRADLEY, Erin, Kathleen; VERNER, Erik; (816 pag.)WO2019/46784; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 19235-89-3, 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 19235-89-3, name is 4-Chloropyridine-2-carbonitrile. This compound has unique chemical properties. The synthetic route is as follows.

2-Acetyl-4-chloropyridine: To a solution of 4-chloro-2-pyridinecarbonitrile (5.35 g, 38.6 mmol) in benzene (50 ml) and ether (50 ml) cooled to 0 C. was added dropwise over 20 min a 2M solution of MeMgI in ether (23 ml, 46.3 mmol). After 0.5 h, the mixture was allowed to warm to ambient temperature, and stirring continued for 2 h. The mixture was cooled to 0 C. and 2M aqueous HCl (100 ml) added. The mixture was made basic with saturated aqueous sodium bicarbonate (~80 ml) and the organic layer separated and dried (MgSO4). After removal of solvent, the residue was purified by flash chromatography eluding with ethyl acetate/hexane (1:5) to afford 3.60 g (60%) of 2-acetyl-4-chloropyridine. 1H-NMR (DMSO-d6) delta: 8.59 (1H, d, J=5.1 Hz), 8.04 (1H, d, J=1.8 Hz), 7.47 (1H, dd, J=1.8, 5.1 Hz), 2.72 (3H, s).

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 19235-89-3, 4-Chloropyridine-2-carbonitrile.

Reference:
Patent; Nakao, Kazunari; Stevens, Rodney William; Kawamura, Kiyoshi; Uchida, Chikara; Koike, Hiroki; Caron, Stephane; US6608070; (2003); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 165547-79-5, 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.165547-79-5, name is 4-Chloro-3-nitro-2(1H)-pyridinone, molecular formula is C5H3ClN2O3, molecular weight is 174.54, as common compound, the synthetic route is as follows.

To a suspension of 4-chloro-3-nitro-2-pyridone (1.0 g, 5.7 mmol) and K2CO3 (1.6 g, 11.5 mmol) in DMA (5 mL) was added Mel (0.72 mL, 11.5 mmol). The rxn mixture was heated to 45C and stirred for 1h. It was quenched with H2O, acidified to pH 5 with a 25% aq. soln. of HCI and extracted with EtOAc (3x). The combined org. phases were washed with brine, dried over MgSCh and concentrated in vacuo. LC-MS: tR=0.60 min ; [M+H]+: 189.15 (0934) 1H NMR (400 MHz, DMSO-d6)5: 8.10 (d, J = 7.4 Hz, 1 H), 6.70 (d, J = 7.4 Hz, 1 H), 3.55 (s, 3 H)

Statistics shows that 165547-79-5 is playing an increasingly important role. we look forward to future research findings about 4-Chloro-3-nitro-2(1H)-pyridinone.

Reference:
Patent; IDORSIA PHARMACEUTICALS LTD; FROIDEVAUX, Sylvie; HUBLER, Francis; MURPHY, Mark; RENNEBERG, Dorte; STAMM, Simon; (188 pag.)WO2019/141803; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1003711-43-0, 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 1003711-43-0, name is 2-Bromo-5-hydroxy-3-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 2-oxazolemethanol (1.12 g, 11.30 mmol, Combi-Blocks Inc.) and triphenylphosphine (3.72 g, 14.18 mmol) in THF (20 mL) was added 2-bromo-5- hydroxy-3-picoline (2.27 g, 12.07 mmol, AOB Chem USA). The mixture was cooled to 0 C and 1 ,2-ethoxycarbonyl diazene (2.5 mL, 13.72 mmol) was added slowly. The solution was slowly allowed to warm to RT. After 21 h, diisopropyl azodicarboxylate (1.5 mL, 7.63 mmol) was added to the mixture. About 1.5 h later, a second batch of diisopropyl azodicarboxylate (1.5 mL, 7.63 mmol) was added. The mixture was stirred at RT for an additional 4 h and was diluted with EtOAc (50 mL). The solution was washed with NaOH (0.5 N, 10 mL), water, brine, and then dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography (10-50% EtOAc in DCM) to afford 2-(((6-bromo-5-methylpyrid in-3-yl)oxy)methyl)oxazole (3.8 g, ~80% pure) as a white solid that contained the hydrazine by-product as impurities (based on 1H-NMR). LCMS (ESI, pos.) 269.0 (M+1 )+. 1H NMR (400 MHz, CHLOROFORM-d) delta 8.02 (d, J=2.93 Hz, 1 H), 7.70 (d, J=0.78 Hz, 1 H), 7.23 (d, J=2.74 Hz, 1 H), 7.17 (s, 1 H), 5.18 (s, 2H), 2.37 (s, 3H).

According to the analysis of related databases, 1003711-43-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AMGEN INC.; ALLEN, Jennifer R.; AMEGADZIE, Albert; BOURBEAU, Matthew P.; BROWN, James A.; CHEN, Jian J.; CHENG, Yuan; FROHN, Michael J.; GUZMAN-PEREZ, Angel; HARRINGTON, Paul E.; LIU, Longbin; LIU, Qingyian; LOW, Jonathan D.; MA, Vu Van; MANNING, James; MINATTI, Ana Elena; NGUYEN, Thomas T.; NISHMURA, Nobuko; NORMAN, Mark H.; PETTUS, Liping H.; PICKRELL, Alexander J.; QIAN, Wenyuan; RUMFELT, Shannon; RZASA, Robert M.; SIEGMUND, Aaron C.; STEC, Markian M.; WHITE, Ryan; XUE, Qiufen; (759 pag.)WO2016/22724; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1190319-62-0, 6-Bromo-1H-pyrrolo[3,2-b]pyridin-2(3H)-one, 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, Computed Properties of C7H5BrN2O, blongs to pyridine-derivatives compound. Computed Properties of C7H5BrN2O

Example 76 Preparation of intermediate E/Z-6-bromo-3-(3-chloro-2-fluoro-benzylidene)-1,3-dihydro-pyrrolo[3,2-b]pyridin-2-one To the mixture of 6-bromo-4-aza-2-oxindole (Sinova, 0.3 g, 1.4 mmol) and 3-chloro-2-fluorobenzaldehyde (Oakwood, 0.45 g, 2.8 mmol) in methanol (20 mL) was added piperidine (Aldrich, 0.36 g, 4.2 mmol) dropwise. The reaction mixture was heated at 50 C. and stirred for 3 h. Then the mixture was cooled to room temperature and filtered. The resulting precipitate was collected and dried to give the first batch of desired product. The filtrate was concentrated, and the residue was purified by chromatography (25-50% EtOAc in hexanes) to give the second batch of product. The two batches were combined to give E/Z-6-bromo-3-(3-chloro-2-fluoro-benzylidene)-1,3-dihydro-pyrrolo[3,2-b]pyridin-2-one as a yellow solid (0.35 g, 70%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1190319-62-0, 6-Bromo-1H-pyrrolo[3,2-b]pyridin-2(3H)-one, and friends who are interested can also refer to it.

Reference:
Patent; Bartkovitz, David Joseph; Chu, Xin-Jie; Ding, Qingjie; Karnachi, Prabha Saba; Liu, Jin-Jun; So, Sung-Sau; Zhang, Jing; Zhang, Zhuming; US2012/46306; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 175204-82-7, Methyl 4-(trifluoromethyl)nicotinate, 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, COA of Formula: C8H6F3NO2, blongs to pyridine-derivatives compound. COA of Formula: C8H6F3NO2

A solution of 0.37 g (9.7 mmoles) of lithium aluminum hydride dissolved in 100 ml of THF was cooled to -50C. Thereto was gradually added dropwise a solution of 2.0 g (9.8 mmoles) of methyl 4-trifluoromethylnicotinate dissolved in 30 ml of THF. The mixture was stirred at -50C for 3 hours to give rise to a reaction. After confirmation of the completion of the reaction, ethyl acetate was added, followed by stirring for a while. Water was added, followed by stirring for a while. The reaction mixture was filtered under vacuum. The filtrate was extracted with ethyl acetate. The resulting organic layer was washed with water and an aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate. The resulting solution was subjected to vacuum distillation to remove the solvent contained therein. The residue was purified by silica gel column chromatography (developing solvent: hexane-ethyl acetate mixed solvent) to obtain 0.6 g (yield: 35.3%) of (4-trifluoromethylpyridin-3-yl)-methanol as a yellow oily substance. 1H-NMR [CDCl3/TMS, delta (ppm)]: 9.00 (1H,s), 8.73 (1H,d), 7.51 (1H,d), 4.95 (2H,s)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,175204-82-7, Methyl 4-(trifluoromethyl)nicotinate, and friends who are interested can also refer to it.

Reference:
Patent; KUMIAI CHEMICAL INDUSTRY CO., LTD.; IHARA CHEMICAL INDUSTRY CO., LTD.; EP1364946; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 150114-71-9, 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 150114-71-9 as follows.

10. Preparation of 4-Amino-3,6-dichloro-5-fluoropyridine-2-carboxylic Acid (Compound 19) To a solution of 4-amino-3,6-dichloropyridine-2-carboxylate (1.5 g, 6.8 mmol) in 20 mL of dry acetonitrile was added 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis (tetrafluoroborate) (Selectfluor from Aldrich Chemical Company, Inc.; 2.9 g, 2.59 mmol [F+]/g). The resulting mixture was heated at reflux for 3 hr, then allowed to cool to room temperature. This material was taken up in Et2O and washed with H2O. The organic layer was dried over MgSO4, filtered and concentrated to yield a brown oil. The crude product was purified via reverse phase HPLC (50% acetonitrile/water) to give 0.37 g of white solid which was stirred in 1N NaOH for 1 hr then made acidic with conc. HCl. The precipitated white solid was collected with suction, washed with H2O and dried under vacuum to give 170 mg of 4-amino-3,6-dichloro-5-fluoropyridine-2-carboxylic acid (11% yield); mp 214 C. dec.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,150114-71-9, its application will become more common.

Reference:
Patent; Dow AgroSciences LLC; US6297197; (2001); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 71670-70-7, 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 71670-70-7, name is 2-(Chloromethyl)-5-methylpyridine hydrochloride. This compound has unique chemical properties. The synthetic route is as follows.

3-fluoro-4-nitrophenol (200.0 g, 1.27 mol) was added to a solution of 2-(chloromethyl)-5-methylpyridine hydrochloride (222 g, 1.25 mol), powdered potassium carbonate (383.6 g, 2.75 mol), potassium iodide (207 g, 1.25 mol), and acetonitrile (3.4 L). The resulting mixture was stirred at 60 Celsius for 2 h. The reaction was cooled to RT, concentrated to dryness and partitioned between H2O (1.5 L) and ethyl acetate (1.5 L). The organic layers were separated and the aqueous layer was extracted with ethyl acetate (1.0 L). The combined organic layers were washed with brine (1 L) then dried over magnesium sulfate, filtered, and concentrated to dryness. The crude solid was recrystallized from i-PrOH (1.5 L) at 70 Celsius. After cooling to 0 Celsius the solid was collected by filtration and rinsed with i-PrOH (2×200 mL) and heptanes (2×200 mL) to yield the title compound as a dark solid (242.0 g, 73.9%). MS (ESI): mass calcd. for C13H11FN2O3, 262.10; m/z found, 263.1 [M+H]+. 1H NMR (400 MHz, DMSO-d6) delta 8.44 (s, 1H), 8.16 (t, J=9.2, 1H), 7.76-7.62 (m, 1H), 7.45 (d, J=7.9, 1H), 7.30 (dd, J=13.7, 2.5, 1H), 7.07 (dd, J=9.3, 1.9, 1H), 5.30 (s, 2H), 2.31 (s, 3H).

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 71670-70-7, 2-(Chloromethyl)-5-methylpyridine hydrochloride.

Reference:
Patent; Chai, Wenying; Dvorak, Curt A.; Eccles, Wendy; Edwards, James P.; Goldberg, Steven D.; Krawczuk, Paul J.; Lebsack, Alec D.; Liu, Jing; Pippel, Daniel J.; Sales, Zachary S.; Tanis, Virginia M.; Tichenor, Mark S.; Wiener, John J. M.; US2014/275029; (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. 887707-23-5, name is 2-Hydroxy-5-iodo-3-(trifluoromethyl)pyridine. A new synthetic method of this compound is introduced below., category: pyridine-derivatives

Then in DMF, 2-hydroxy-3-trifluoromethyl-5- (iodo) pyridine I wasmixed with POCl3, and was heated for 20 minutes in a microwave at130 C, and 2-chloro-3-trifluoromethyl -5 – (iodo) pyridine J (yield of 50% to55%) is formed.

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, 887707-23-5, 2-Hydroxy-5-iodo-3-(trifluoromethyl)pyridine.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; JUNG, MICHAEL E; SAWYERS, CHARLES L; OUK, SAMEDY; TRAN, CHRIS; WONGVIPAT, JOHN; (40 pag.)JP2016/11315; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem