Category: pyridine-derivatives

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. 111770-86-6, name is 5-Bromo-2-ethynylpyridine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 111770-86-6

(Azidomethyl)trimethylsilane (0.6 mL, 4.0 mmol) was added to Intermediate 41 (500 mg, 2.76 mmol) in toluene (10 mL), and the reaction mixture was warmed up to 80 C. and stirred o.n. Solvent was removed under vacuum and the residue was purified by column chromatography (petroleum ether_EtOAc=6:1). The product was obtained as a yellow solid. MS (m/z): 311, 313 [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, 111770-86-6, 5-Bromo-2-ethynylpyridine.

Reference:
Patent; Gordeev, Mikhail Fedorovich; Yuan, Zhengyu; Liu, Jinqian; Wang, Qiang; US2010/69441; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 14150-94-8, 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 14150-94-8, name is 1-Methyl-3,5-dinitro-1H-pyridin-2-one. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of (+/-)- 1 ‘- { [2-(trimethylsilyl)ethoxy]methyl} -3H-spiro[cyclopentane- l,3′-pyrrolo[2,3-]pyridine]-2’,3(l’H)-dione from Step A (230 mg, 0.692 mmol) and 1-methyl- 3,5-dinitropyridin-2(lH)-one (173 mg, 0.869 mmol) [Tohda et al. (1990) Bull. Chem. Soc. Japan 63, 2820] in 2 M ammonia in MeOH (3.5 mL) was heated to reflux for 18 h. The mixture was concentrated in vacuo and purified by silica gel chromatography, eluting with a gradient of hexane:EtOAc – 100:0 to 50:50, to give the title compound. MS: mlz = 413 (M + 1).

According to the analysis of related databases, 14150-94-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK & CO., INC.; WO2008/73251; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 156118-16-0, 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 156118-16-0, name is 3-Amino-6-bromo-4-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

Step 2 [0612] To a suspension 6-bromo-4-methylpyridin-3 -amine (XV) (186 g, 994 mmol, 1.00 eq) and KOAc (115 g, 1.17 mol, 1.18 eq) in CHC13 (3.50 L) was added Ac20 (405 g, 3.97 mol, 3.99 eq) and the suspension was stirred at 25C for 1 h and then heated at 60-70C to reflux for an additional 2 h. After cooling the suspension to 25C, isopentyl nitrate (233 g, 1.99 mol, 2.00 eq) and 18-crown-6 (21 g, 79.5 mmol, 0.08 eq) was added and the suspension heated to reflux for 12 h. After cooling to 25C, the suspension was filtered and the filtrate was concentrated under reduced pressure to yield a residue that was treated with a suspension of potassium carbonate (450 g) in a solution of methanol and water (450 mL) at 0C for 3 h. The suspension was concentrated under reduced pressure to yield a residue that was extracted with EtOAc (1000 mL x 3) and washed with brine. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure to give 5-bromo-lH-pyrazolo[3,4-c]pyridine (XVI) (200 g, crude) as yellow solid. The crude product was used for the next step without any purification. NMR (DMSO- tf, 400 MHz) delta ppm 7.96 (s, 1H), 8.15 (s, 1H), 8.86 (s, 1H); ESIMS found for C6H4BrN3 mlz 198.3 (M+H).

According to the analysis of related databases, 156118-16-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SAMUMED, LLC.; KC, Sunil Kumar; WALLACE, David Mark; CAO, Jianguo; CHIRUTA, Chandramouli; HOOD, John; (254 pag.)WO2017/23980; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 60290-21-3, 4-Chloro-1H-pyrrolo[3,2-c]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, COA of Formula: C7H5ClN2, blongs to pyridine-derivatives compound. COA of Formula: C7H5ClN2

General procedure: To a solution of 4-chloro-lH-pyrrolo-[3,2-c]-pyridine [60290-21-3] (2.0 g, 13.1 mmol) dissolved in DMF (30.5 mL, 0.944 g/mL, 393.2 mmol) at 0C was added portionwise sodium hydride (1.1 g, 28.8 mmol). The reaction mixture was allowed to reach rt and stirred 45 min, after which it was re-cooled to 0C and l-bromobutane (2.1 mL, 1.27 g/mL, 19.7 mmol) was added dropwise. The mixture was then allowed to reach rt and stirred overnight. NaHC03 sat solution was added and the aqueous phase was extracted with EtOAc. The combined organic extracts were washed with water and brine, then dried over MgS04 and concentrated in vacuo. The crude residue was purified by column chromatography (silica gel; gradient Heptane/EtOAc from 100/0 to 50 /50) to yield 1-1 (2.7 g, 98.7%) as a yellow liquid

The synthetic route of 60290-21-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BARTOLOME-NEBREDA, Jose Manuel; TRABANCO-SUAREZ, Andres, Avelino; TRESADERN, Gary John; MARTINEZ LAMENCA, Carolina; LEENAERTS, Joseph Elisabeth; OEHLRICH, Daniel; BUIJNSTERS, Peter Jacobus Johannes Antonius; VELTER, Adriana, Ingrid; VAN ROOSBROECK, Yves, Emiel, Maria; (171 pag.)WO2019/243535; (2019); 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.1196073-28-5, name is Methyl 4,6-dichloro-2-methylnicotinate, molecular formula is C8H7Cl2NO2, molecular weight is 220.05, as common compound, the synthetic route is as follows.Quality Control of Methyl 4,6-dichloro-2-methylnicotinate

To a stirred suspension of sodium hydride (60% in mineral oil, 85 mg, 2.14 mmol) in DMF (4 mL) was added, dropwise, ethyleneglycol mono t-butyl ether (278 mg, 2.35 mmol). the reaction mixture was stirred for 25 min. A solution of 4,6-dichloro-2-methyl- nicotinic acid methylester (0.5g, 2.14 mmol) in DMF (1.5 mL) was added to the reaction mixture was stirred at RT overnight. The reaction mixture was quenched with water, extracted with EtOAc, the organic layer washed with water, brine, dried over Na2SO4 and volatiles removed. The residue was purified by column chromatography using 0-50% EtOAc/Hexanes to provide compound Villa (260 mg).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1196073-28-5, Methyl 4,6-dichloro-2-methylnicotinate, and friends who are interested can also refer to it.

Reference:
Patent; THRESHOLD PHARMACEUTICALS, INC.; WO2009/140553; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 54189-82-1, 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. 54189-82-1, name is 6-Chloro-N-methylnicotinamide, molecular formula is C7H7ClN2O, 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.

Example 101 Preparation of N-Methyl-6-(1-oxo-2-(2-(pyrrolidin-1-yl)ethyl)-1,2,3,4-tetrahydro-isoquinolin-6-yloxy)nicotinamide hydrochloride A suspension of NaH (60% dispersion in mineral oil, 0.06 g, 5.4 mmol) in DMF at room temperature was treated dropwise over a 15 min period with a solution of 6-hydroxy-2-(2-(pyrrolidin-1-yl)ethyl)-3,4-dihydroisoquinolin-1(2H)-one (0.2 g, 2.7 mmol) in DMF, stirred at room temperature for 30 min, treated with a solution of 6-chloro-n-methylnicotinamide in DMF, heated at 100 C. overnight, cooled to room temperature, diluted with water and extracted with CH2Cl2. The combined extracts were washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by ISCO CombiFlash chromatography (silica, 0-15% methanol in methylene plus 0.5% ammonium hydroxide) to afford the free amine of the title product as a colorless oil. The oil was dissolved in ethanol, treated with ethereal HCl, stirred and filtered. The filtercake was washed with ether and dried to provide the title compound as a white solid, 30 mg (10%), mp 228-230 C.; identified by NMR and mass spectral analyses. MS (ES) m/z 395.2 [M+H]+.

According to the analysis of related databases, 54189-82-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Wyeth; US2009/69300; (2009); 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. 13194-60-0, name is 3-Chloro-4-nitropyridine. A new synthetic method of this compound is introduced below., Computed Properties of C5H3ClN2O2

3-chloro-4-nitropyridine (5 g, 31.63 mmol), 3-pyridineboronic acid (3 g, 37.75 mmol) was added to a 500 ml single-necked flask.50 ml of a 2 M potassium carbonate aqueous solution was dissolved in a solvent of 50 ml of ethanol and 100 ml of toluene.Under the protection of N2, PdCl2(PPh3)2 (0.75 g, 0.98 mmol) was added. The temperature was slowly raised to 100 C, and the mixture was reacted under reflux for 24 hours.After cooling, the layers were separated, and the organic layer was evaporated, and then, with petroleum ether and ethyl acetate (1.5:1).4.5 g of a pale yellow solid were obtained in a yield of 60%.

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, 13194-60-0, 3-Chloro-4-nitropyridine.

Reference:
Patent; Wuhan Shang Sai Optoelectric Technology Co., Ltd.; Mu Guangyuan; Zhuang Shaoqing; Ye Shaofeng; (96 pag.)CN109422743; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 121912-29-6, 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. 121912-29-6, name is Ethyl 1-(pyridin-4-yl)piperidine-4-carboxylate. A new synthetic method of this compound is introduced below.

Step 2: Synthesis of 1-(4-pyridyl)-4-piperidinecarboxylic acid hydrochloride: 2.95 g (12.6 mmol) of ethyl 1-(4-pyridyl)-piperidine-4-carboxylate was stirred in 100 ml of dioxane. After adding 50 ml of 1 N hydrochloric acid, the obtained mixture was stirred at 95C for 20 hours. The solventwas evaporated under reduced pressure to obtain the title compound. Yield: 3.21 g (11.5 mmol) (91 %) MS (ESI, m/z) 207 (MH+) H-NMR (DMSO-d6) delta 1.54 (2H, t), 1.90 (2H, d), 2.60-2.70 (1H, m), 3.30 (2H, t), 4.10 (2H, d), 7.19 (2H, d), 8.20 (2H, d)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,121912-29-6, Ethyl 1-(pyridin-4-yl)piperidine-4-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Ajinomoto Co., Inc.; EP1065200; (2001); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 851386-31-7, 2,3-Difluoroisonicotinic 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, 851386-31-7, blongs to pyridine-derivatives compound. Product Details of 851386-31-7

2,2,2-trifluoroacetic anhydride (7.97 g, 37.9 mmol) was added to a stirred mixture of 2,3-difluoroisonicotinamide (3.00 g, 19.0 mmol), and triethylamine (5.76 g, 56.9 mmol) in DCM (30 mL) at15 C, and the resulting mixture was stirred at 15 C for 17 h. The mixture was diluted with H20 (50 mL). The water layer was extracted with DCM (40 mLx3). The combined organic layers were washed with brine (50 mL), dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by Si02 column chromatography (heptane: EtOAc = 95:5 to 40:60) to give 2,3- difluoroisonicotinonitrile as a solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,851386-31-7, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WALJI, Abbas; BERGER, Richard; STUMP, Craig, A.; SCHLEGEL, Kelly Ann, S.; MULHEARN, James, J.; GRESHOCK, Thomas, J.; FRALEY, Mark, E.; JONES, Kristen, G.; (139 pag.)WO2017/222952; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 884494-36-4, 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. 884494-36-4, name is 3-Bromo-2-chloro-5-fluoropyridine, molecular formula is C5H2BrClFN, 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.

To a solution of urea compound with hydrogen peroxide (1 : 1) (1.34, 14.3 mole) and trifluoroacetic anhydride (2 mL, 14.3 mole) in 10 mL dichloromethane at 0 C for at least 15 minutes was added 3- fluoro-5-bromopicolinonitrile (500 mg, 2.38 mmol). The reaction mixture was stirred at 40 C for 2 hours. The reaction quenched with saturated aqueous NaHC03 (20 mL) and then extracted with DCM (20 mL x 5). The combined organics were dried over anhydrous Na2SC”4 and concentrated to give the crude title compound, which was carried forward without purification. MS: 226, 228 (M+l).

According to the analysis of related databases, 884494-36-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MSD R&D (CHINA) CO., LTD.; ACTON, John, J., III; BAO, Jianming; DENG, Qiaolin; EGBERTSON, Melissa; FERGUSON, Ronald, III; GAO, Xiaolei; HARRISON, Scott Timothy; KNOWLES, Sandra, L.; LI, Chunsing; LO, Michael Man-Chu; MAZZOLA, Robert, D., Jr.; MENG, Zhaoyang; NA, Meng; RUDD, Michael, T.; SELYUTIN, Oleg, B.; TELLERS, David, M.; TONG, Ling; ZHANG, Fengqi; (195 pag.)WO2019/5587; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem