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. 148038-83-9, name is 6-Bromo-1H-imidazo[4,5-b]pyridin-2(3H)-one. This compound has unique chemical properties. The synthetic route is as follows. Formula: C6H4BrN3O

General procedure: 145 (210mg, 1.41mmol) was dissolved in POCl3 (4mL) and stirred at reflux for 12h. The mixture was concentrated, and the residue was dissolved in EtOAc (30mL). The organic layer was then washed successively with saturated NaHCO3 (2×20mL), water (20mL) and brine (20mL), dried with Na2SO4 and concentrated. The crude residue was then purified by column chromatography (100% CyHex to 80% EtOAc/CyHex) to obtain the 146 as a solid (71mg, 30%).

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, 148038-83-9, 6-Bromo-1H-imidazo[4,5-b]pyridin-2(3H)-one.

Reference:
Article; Blackmore, Timothy R.; Jacobson, Jonathan; Jarman, Kate E.; Lewin, Sharon R.; Nguyen, William; Purcell, Damian F.; Sabroux, Helene Jousset; Sleebs, Brad E.; European Journal of Medicinal Chemistry; vol. 195; (2020);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 75308-46-2, tert-Butyl 2,6-dichloroisonicotinate, 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, SDS of cas: 75308-46-2, blongs to pyridine-derivatives compound. SDS of cas: 75308-46-2

To a solution of tert-butyl 2,6-dichloroisonicotinate (1 1.0 g, 44.3 mmol) in ethanol (222 mL) was added hydrazine hydrate (6.46 mL, 133 mmol). The mixture was heated 75 0C. After 18 h, the mixture was cooled to ambient temperature. The mixture was concentrate down to half of the volume. The solid crashed out was filtered off and the filtrate was concentrated to dryness: LC-MS [M+l] = 244.1.

The synthetic route of 75308-46-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP &; DOHME CORP.; BURGEY, Christopher, S.; DENG, Zhengwu, J.; NGUYEN, Diem, N.; PAONE, Daniel, V.; POTTEIGER, Craig, M.; STAUFFER, Shaun, R.; SEGERDELL, Carolyn; NOMLAND, Ashley; LIM, John, J.; WO2010/111058; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1121-76-2, 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.1121-76-2, name is 4-Chloropyridine 1-oxide, molecular formula is C5H4ClNO, molecular weight is 129.5444, as common compound, the synthetic route is as follows.

4-Chloro-2-(hydroxymethyl)pyridine : A solution of 4-CHLOROPYRIDINE ASOXIDE (5 G, 38.6 MMOL) and TRIMETHYLOXONIUM TETRAFLUOROBORATE (5.94 G, 40.1 MMOI) in CH2CL2 (115 mL) was stirred for two hours at ambient temperature. The solvent was evaporated and the residue taken up in MeOH (115 mL) and heated to near boiling. Ammonium persulfate (1.76 G, 7.72 MMOL) dissolved in H2O (7.7 mL) was added and the mixture was heated to reflux for 30 min. A second portion of ammonium persulfate (0.88 G) in H2O (3.9 mL) was added and the mixture was refluxed for another 30 min. The solvent was evaporated and the residue was partitioned between CHZCTZ and aqueous Na2CO3 (10% w/v). The organic layer was washed with H2O, dried over MgSO4 and evaporated leaving 2.4 G (43%) of the title compound. 1H NMR (CDC13) 8 8.20 (d, 1H, J=5. 0 Hz, H-6); 7.31 (s, 1H, H-3); 7.04 (d, 1H, J=5. 0 Hz, H-5); 5.46 (s, LH, OH); 4.61 (s, 2H, CH2).

Statistics shows that 1121-76-2 is playing an increasingly important role. we look forward to future research findings about 4-Chloropyridine 1-oxide.

Reference:
Patent; TRIGEN LIMITED; WO2005/12323; (2005); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 106047-29-4, Adding some certain compound to certain chemical reactions, such as: 106047-29-4, name is 6-Bromo-2,4′-bipyridine,molecular formula is C10H7BrN2, 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 106047-29-4.

Synthesis of Compound 1; 6.0 g (12.63 mmol) of Intermediate 1c and 2.7 g (11.48 mmol) of Intermediate 1d were added to a mixed solvent of 4.76 g (34.4 mmol) potassium carbonate solution and THF, 398 mg (3 mol%) of Pd(PPh3)4 was added thereto while stirring, and the mixture was heated for 12 hours. The mixture was cooled to room temperature and subjected to extraction using dichloromethane. Then, an organic layer was collected, and the solvent was removed by drying the organic layer using anhydrous magnesium sulfate under reduced pressure. The resulting product was filtered using column chromatography (ethyl acetate_dichloromethane=3:7) to obtain 5.3 g of yellow solid Compound 1 (Yield: 80%). 1H NMR (500MHz, CDCl3) delta 8.73(d, 1H), 8.49(d, 1H), 8.18-8.10(m, 5H), 8.05(dd, 2H), 8.01(d, 1H), 7.97(d, 1H), 7.88(d, 1H), 7.84(m, 1H), 7.80-7.62(m, 13H), and 7.36(dd, 2H).

According to the analysis of related databases, 106047-29-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Samsung Mobile Display Co., Ltd.; EP2110373; (2009); 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.162102-79-6, name is Dimethyl 4-bromopyridine-2,6-dicarboxylate, molecular formula is C9H8BrNO4, molecular weight is 274.07, as common compound, the synthetic route is as follows.Recommanded Product: Dimethyl 4-bromopyridine-2,6-dicarboxylate

Under nitrogen protection, add 4-bromopyridine-2,6-dicarboxylic acid dimethyl ester Ia (1.0equiv) and IIa (2.0equiv) to a 50mL round bottom flask, and then add N, N-dimethylformamide to dissolve.Then, 10% catalytic amount of tetrabutylammonium bromide was added, and the reaction was performed under reflux for 12 hours, followed by post-treatment: 30 mL of water was added, extracted with ethyl acetate, dried over anhydrous sodium sulfate, and then subjected to column chromatography. To white solid IIIa, yield 87%.Then under the protection of nitrogen, add IIIa and 2.2equivs L-phenylglycinol to the sealed tube,Stir overnight at 100 C without solvent (the reaction is complete by TLC),Direct column chromatography gave white solid IVa in 99% yield.Then add IVa to the Schlenk bottle and then add anhydrous dichloromethane.Add 2.2 equivs diethylamine sulfur trifluoride reagent dropwise at -20 C, stir the reaction overnight, add 10% ammonia water to quench the reaction, add dichloromethane and water to extract 3 times, and dry with anhydrous sodium sulfate Column chromatography gave S1 as a white solid with a yield of 67%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,162102-79-6, Dimethyl 4-bromopyridine-2,6-dicarboxylate, and friends who are interested can also refer to it.

Reference:
Patent; East China Normal University; Zhou Jian; Wang Cai; Liao Kui; Zhou Feng; (23 pag.)CN110305122; (2019); A;,
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. 75903-58-1, name is 6-Aminopyridine-2-sulfonamide, the common compound, a new synthetic route is introduced below. COA of Formula: C5H7N3O2S

6-(3-fluoro-5-isobutoxy-phenyl)-2-(3,5,5-trimethylcyclopenten-1-yl)pyridine-3-carboxylic acid (74 mg, 0.19 mmol) and CDI (45 mg, 0.28 mmol) were mixed in DMF (740 muL) under and atmosphere of nitrogen and the reaction mixture was heated to 45 C. for 45 minutes. In a separate vial, 6-aminopyridine-2-sulfonamide (80.62 mg, 0.4655 mmol) and NaH (18 mg, 0.46 mmol) were mixed slowly in DMF (370.0 muL) and mixture was heated to 45 C. for 45 minutes. The 6-aminopyridine-2-sulfonamide reaction mixture was added to the activated acid and the reaction mixture was heated at 50 C. for 16 h. The reaction mixture was filtered and then purified directly by reverse-phase preparative chromatography utilizing a C18 column and HPLC-MS method 10-99% mobile phase B (mobile phase A=water (de-ionized, no acid modifier), mobile phase B=acetonitrile) to afford N-[(6-amino-2-pyridyl)sulfonyl]-6-(3-fluoro-5-isobutoxy-phenyl)-2-(3,5,5-trimethylcyclopenten-1-yl)pyridine-3-carboxamide (Compound 2081) (Compound 2039) (64 mg, 62%) as an off-white solid, ESI-MS m/z calc. 552.22064. found 553.4 (M+1)+. Retention time: 2.25 minutes; 1H NMR (400 MHz, DMSO) delta 12.55 (s, 1H), 7.96 (d, J=8.2 Hz, 1H), 7.86 (d, J=8.2 Hz, 1H), 7.68-7.60 (m, 1H), 7.56 (s, 1H), 7.49 (d, J=9.6 Hz, 1H), 7.20 (d, J=7.3 Hz, 1H), 7.01-6.84 (m, 1H), 6.72 (d, J=8.4 Hz, 1H), 6.55 (s, 2H), 5.62 (d, J=1.7 Hz, 1H), 3.85 (d, J=6.6 Hz, 2H), 2.66 (ddd, J=14.3, 7.4, 1.8 Hz, 1H), 2.03 (dd, J=13.2, 6.6 Hz, 1H), 1.95 (dd, J=12.1, 7.5 Hz, 1H), 1.38-1.28 (m, 4H), 1.25 (s, 3H), 0.99 (d, J=6.7 Hz, 6H), 0.93 (d, J=6.9 Hz, 3H).

The synthetic route of 75903-58-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; Miller, Mark Thomas; Anderson, Corey; Arumugam, Vijayalaksmi; Bear, Brian Richard; Binch, Hayley Marie; Clemens, Jeremy J.; Cleveland, Thomas; Conroy, Erica; Coon, Timothy Richard; Frieman, Bryan A.; Grootenhuis, Peter Diederik Jan; Gross, Raymond Stanley; Hadida-Ruah, Sara Sabina; Haripada, Khatuya; Joshi, Pramod Virupax; Krenitsky, Paul John; Lin, Chun-Chieh; Marelius, Gulin Erdgogan; Melillo, Vito; McCartney, Jason; Nicholls, Georgia McGaughey; Pierre, Fabrice Jean Denis; Silina, Alina; Termin, Andreas P.; Uy, Johnny; Zhou, Jinglan; (590 pag.)US2016/95858; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 870065-73-9, Adding some certain compound to certain chemical reactions, such as: 870065-73-9, name is 2,5,6-Trifluoronicotinonitrile,molecular formula is C6HF3N2, 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 870065-73-9.

A solution of 1.04 M KOtBu in t-BuOH (110 mL, 114 mmol) pre-mixed with THF (20 mL) was added dropwise over 15 min to a stirred 0 C. solution of 2,5,6-trifluoro-nicotinonitrile (16.0 g, 101 mmol) contaminated with an additional 4.6 g DMSO, as prepared in the preceding step, in t-BuOH (80 mL) and THF (15 mL; to prevent freezing). The resulting homogeneous reddish-amber solution was stirred for an additional 5 min at 0 C., the ice bath was then removed, and the solution stirred for an addititional 20 min at rt. The reaction was then quenched with 5 M NH4Cl (100 mL) and extracted with ether (2×100 mL). The combined organic layers were washed with water (1×100 mL), 1 M NaCl (1×150 mL), and 4 M NaCl (1×100 mL), and the clear purple organic layer was dried (Na2SO4), concentrated under reduced pressure, taken up in ether (50 mL), and filtered through a pad of diatomaceous earth. The filter cake was washed with ether (3×50 mL), and the combined filtrates were concentrated under reduced pressure at 50-60 C. to afford 20.89 g of a clear purple oil. NMR indicated an 89:11 mol ratio of the title compound and 2,6-di-tert-butoxy-5-fluoro-nicotinonitrile (18.22 g title compound; 85%). 1H-NMR (300 MHz, CDCl3) delta 7.60 (dd, 1H), 1.67 (s, 9H)

According to the analysis of related databases, 870065-73-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Kreutter, Kevin; Lu, Tianbao; Lee, Yu Kai; Teleha, Christopher; Player, Mark; Zhu, Xizhen; US2006/241148; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 932-35-4, Adding some certain compound to certain chemical reactions, such as: 932-35-4, name is 3-Hydroxypicolinonitrile,molecular formula is C6H4N2O, 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 932-35-4.

In a round-bottom flask, mix 1.8 g (0.015 mol) of 3-hydroxypridine-2- carbonitrile, 30 ml of DMF, 9.77 g (0.30 mol) of Cs2CO3 and 2.54 g (0.018 mol) of 1-fluoro-4-nitrobenzene. Heat the reaction mass to 140 and stir at this temperature for 4 h; use the TLC method to ensure the completeness of the reaction. Distill off the solvent under redused pressure and add 40 mL of water. Filter the precipitate, wash with 15 ml of water and 15 ml of hexane. Yield: 2.86 g (79%).

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. 932-35-4, 3-Hydroxypicolinonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JOINT STOCK COMPANY “BIOCAD”; GAVRILOV, Aleksey Sergeevich; ALESHUNIN, Pavel Aleksandrovich; GORBUNOVA, Svetlana Leonidovna; REKHARSKY, Mikhail Vladimirovich; KOZHEMYAKINA, Natalia Vladimirovna; KUKUSHKINA, Anna Aleksandrovna; KUSHAKOVA, Anna Sergeevna; MIKHAYLOV, Leonid Evgen`evich; MOLDAVSKY, Alexander; POPKOVA, Aleksandra Vladimirovna; SILONOV, Sergey Aleksandrovich; SMIRNOVA, Svetlana Sergeevna; IAKOVLEV, Pavel Andreevich; (197 pag.)WO2018/92047; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 918516-27-5, 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. 918516-27-5, name is 5-(4-Chlorophenyl)-1H-pyrrolo[2,3-b]pyridine, molecular formula is C13H9ClN2, 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.

AICI3 (1.18 g, 8.87 mmol) was added to DCM (40 mL) and the mixture was stirred for 10 min at RT followed by cooling to 0C. 5-(4-chlorophenyl)-1 H-pyrrolo[2,3-b]pyridine (2) (1 eq., 405.92 mg, 1.77 mmol) was added and the mixture was stirred for 30 min then warmed to RT for 3 h. solution A was slowly added to the above suspension at 0 C and the reaction was stirred for 2 days at RT. After complete conversion, the reaction was quenched with methanol (MeOH, 10 mL) and concentrated to give a dark brown residue. Cold water (50 mL) was added to the residue and the pH of the solution was adjusted to 7 (neutral) with aq. ammonia. EtOAc (50 mL) was added and the mixture was stirred for 30 min. It was then filtered through celite, the filtrate was extracted with EtOAc (20 mL x 3) and the combined organic layers were washed with brine, dried over anhydrous Na2S04 and concentrated under reduced pressure to get crude N-(2,4-dibromo-3-(5-(4-chlorophenyl)-1 H-pyrrolo[2,3- b]pyridine-3-carbonyl)-phenyl)propane-1 -sulfonamide (900 mg, crude) which was used in the next step without further purification.

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 918516-27-5, 5-(4-Chlorophenyl)-1H-pyrrolo[2,3-b]pyridine.

Reference:
Patent; HEPAREGENIX GMBH; ALBRECHT, Wolfgang; LAUFER, Stefan; SELIG, Roland; KLOeVEKORN, Phillip; PRAeFKE, Bent; (187 pag.)WO2020/16243; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 4487-57-4, 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 4487-57-4, name is 2,4-Dibromo-5-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows.

2-Bromo-5-nitropyridin-4-amine (Compound 63) To a solution of 2,4-dibromo-5-nitropyridine (200 mg, 0.709 mmol) and triethylamine (0.2 ml, 1.419 mmol) in THF 7 M ammonia (0.2 ml, 1.419 mmol) was added and stirred at room temperature for 24 h. Solvents were removed and the crude was purified by combiflash SiO2 chromatography (0-50% EtOAc-hexanes) to give 2-bromo-5-nitropyridin-4-amine (135 mg, 87%) as a tan solid. 1H-NMR (400 MHz, CD3OD) delta ppm 8.82 (s, 1H), 7.11 (s, 1H); m/z 219.69 (M+H)+.

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 4487-57-4, 2,4-Dibromo-5-nitropyridine.

Reference:
Patent; Stingray Therapeutics, Inc.; The University of Utah; Vankayalapati, Hariprasad; Liu, Xiaohui; Ramamoorthy, Gurusankar; Sharma, Sunil; Kaadige, Mohan Rao; Weston, Alexis; Thode, Trason; (59 pag.)US2019/31655; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem