Category: pyridine-derivatives

Related Products of 669066-93-7, 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 669066-93-7 as follows.

To a solution of the compound [172-1] obtained in the process (1) (426 mg) in ethylene glycol (2.1 mL) was added hydrazine monohydrate (197 muL) at room temperature, and then the reaction mixture was stirred at 140C for 23 hours. After cooling to room temperature, to the reaction mixture was added water, and extracted with a mixed solution of chloroform/isopropanol (volume ratio 10/1). The obtained organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the titled compound (275 mg) as a yellow solid. 1H-NMR (400 MHz, CDCl3) delta: 10.17 (1H, br), 8.65 (1H, d, J = 1.7 Hz), 8.31 (1H, s), 8.04 (1H, s). ESI-MS found: 198 [M+H]+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,669066-93-7, its application will become more common.

Reference:
Patent; Sato Pharmaceutical Co., Ltd.; NAGAI Keita; NAGASAWA Koh; TAKAHASHI Hirobumi; BABA Motoaki; FUJIOKA Shinichi; KONDOH Eri; TANAKA Kenichi; ITOH Yoshiki; EP2669270; (2013); 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. 98-98-6, name is Picolinic acid. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: Picolinic acid

General procedure: A mixture of o-phenylendiamine (1 eq) and the corresponding picolinic acid (1 eq), and 5-20 eq of polyphosphoric acid was stirred in an oil bath at 170 C for 4 h. The mixture was cooled to 100 C and then poured into rapidly stirred water. The pH was adjusted to 7 with NaHCO3. The solid was collected by filtration, and recrystallized from EtOAc to afford the corresponding products with 60-80% yields.

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, 98-98-6, Picolinic acid.

Reference:
Article; Jia, Jianhuan; Jiang, Chenglin; Zhang, Xiaojing; Jiang, Yongwen; Ma, Dawei; Tetrahedron Letters; vol. 52; 43; (2011); p. 5593 – 5595;,
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.1597-32-6, name is 2-Amino-6-fluoropyridine, molecular formula is C5H5FN2, molecular weight is 112.11, as common compound, the synthetic route is as follows.HPLC of Formula: C5H5FN2

General procedure: A dried glass reaction tube equipped with a magnetic stir bar was charged with 1 (106 mg, 0.5 mmol), 2 or 4 (141.2 mg, or 207 mg,1.5 mmol), I2 (254 mg, 1 mmol) in DCE (10 mL); stirred at 100 C for30 min. The solvent was evaporated under vacuum, and washed with saturated sodium thiosulfate solution, water, brine. The organic layer was dried over anhydrous Na2SO4, filtered, and concentrated to give the crude product, which was purified through flash column chromatography (ethyl acetate in petroleum ether) to give the desired product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1597-32-6, 2-Amino-6-fluoropyridine, and friends who are interested can also refer to it.

Reference:
Article; Guo, Yanchun; Wang, Yuexiu; Xue, Han; Cao, Shuxia; Zhao, Yufen; Tetrahedron; vol. 75; 11; (2019); p. 1481 – 1491;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 885500-55-0, Ethyl 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylate, 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, 885500-55-0, blongs to pyridine-derivatives compound. COA of Formula: C10H9ClN2O2

Preparation 14 To a solution of ethyl 4-chloro-1H-pyrrolo[2,3-b]-pyridine-5-caboxylate (2 g) in DMF (20 mL) was added NaH (60% dispersion in oil, 427 mg) at 5C. After the reaction mixture was stirred at ambient temperature for 1 hour, [2-(chloromethoxy)ethyl]-(trimethyl)silane (1.72 mL) was added, and the mixture was stirred at ambient temperature for additional 2 hours. After the reaction mixture was diluted with EtOAc (50 mL), the solution was washed with saturated NaHCO3 aqueous solution (50 mL) and brine (50 mL) successively. After the organic layer was dried over anhydrous MgSO4, filtered and evaporated in vacuo. The residue was purified by silica gel column chromatography (n-hexane) to afford ethyl 4-chloro-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridine-5-caboxylate (2. 91 g) as a colorless viscous liquid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,885500-55-0, its application will become more common.

Reference:
Patent; Astellas Pharma Inc.; EP2123651; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 871836-51-0 , The common heterocyclic compound, 871836-51-0, name is 4-Chloro-1H-pyrazolo[4,3-c]pyridine, molecular formula is C6H4ClN3, 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.

10152] A mixture of tert-butyl 4-chloro-1H-pyrazolo[4,3- c]pyridine (30.6 mg, 0.2 mmol) and E-001 (68 mg, 0.2 mmol) was heated at 1000 C. overnight. MeOH (2 mE) was added and the resultant was purified by Prep-TEC (ethyl acetate petroleum ether=11) to give D-01-02 (50 mg, 54.5percent) as a yellow oil.

The synthetic route of 871836-51-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. Hoffmann-La Roche AG; Savira pharmaceuticals GmbH; European Molecular Biology Laboratory; Schulz-Gasch, Tanja; Weikert, Robert; Neidhart, Werner; Buschmann, Helmut; Szolar, Oliver; Wolkerstorfer, Andrea; Handler, Norbert; Roch, Franz-Ferdinand; Cusack, Stephen; (69 pag.)US2016/2227; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 886365-28-2, Methyl 5-bromo-2-chloroisonicotinate, 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, name: Methyl 5-bromo-2-chloroisonicotinate, blongs to pyridine-derivatives compound. name: Methyl 5-bromo-2-chloroisonicotinate

To a mixture of methyl 5-bromo-2-chloroisonicotinate (10 g, 39.9 mmol) and Pd(Ph3P)4(4.61 g, 3.99 mmol) in THF (100 mL) was added trimethylaluminum (26.0 mL, 51.9 mmol) at 25C. The mixture was then heated to and stirred at 80 C for 6 h. Water (5 mL) was added toquench the reaction and the mixture was concentrated in vacuum. The residue was purified by flash silica gel chromatography (eluting with ethyl acetate/pet. ether gradient) to give methyl 2- chloro-5-methylisonicotinate as a colorless oil. MS: 186 (M + 1). ?HNMR (400 MHz, CDC13) 8.29 (s, 1H), 7.70 (s, 1H), 3.91 (s, 3H), 2.49 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,886365-28-2, Methyl 5-bromo-2-chloroisonicotinate, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; CTXT PTY. LTD.; MACHACEK, Michelle, R.; WITTER, David, J.; REUTERSHAN, Michael Hale; ALTMAN, Michael, D.; STUPPLE, Paul Anthony; (67 pag.)WO2019/94311; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 13534-97-9, 6-Bromopyridin-3-amine, 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, Application In Synthesis of 6-Bromopyridin-3-amine, blongs to pyridine-derivatives compound. Application In Synthesis of 6-Bromopyridin-3-amine

To a solution of 6-bromopyridin-3-amine (4.0 g, 23.25 mmol) in DCM (60 mL) was added pyridine (5.51 g, 69.75 mmol) and 3-chloropropanoyl chloride (3.515 g, 27.9 mmol) at 0°C and allowed to stir at RT for 12. The reaction mixture was diluted with DCM (200 mL) and washed with water (100 mL) and brine solution (100 mL). (0601) The separated organic layer was dried over anhydrous NBISOA, filtered and concentrated under reduced pressure to afford the title compound (4.5 g, 73percent) as a brown colour liquid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,13534-97-9, 6-Bromopyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; ORYZON GENOMICS, S.A.; CARCELLER GONZALEZ, Elena; ORTEGA MUNOZ, Alberto; SALAS SOLANA, Jorge; (129 pag.)WO2018/219478; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 189278-27-1, 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. 189278-27-1, name is 2-Bromo-6-(trifluoromethyl)pyridine, molecular formula is C6H3BrF3N, 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 30 (3aR,4R,6aS)-2-[6-(trifluoromethyl)pyridin-2-yl]octahydrocyclopenta[c]pyrrol-4-ol (3aR,4R,6aS)-Octahydrocyclopenta[c]pyrrol-4-ol (1.65 g, 12.97 mmol) from Example 29, 2-bromo-6-(trifluoromethyl)pyridine (3.66 g, 16.22 mmol) and triethylamine (7.23 mL, 51.9 mmol) were combined in ethanol (7.23 mL). The reaction was heated at 80 C. for 24 hours and the solvent was concentrated in vacuo. The resulting residue was purified by silica gel chromatography using 0-40% ethyl acetate/hexane as eluent to give the title compound and the title compound of Example 31: 1H NMR (500 MHz, pyridine-d5) delta ppm 7.47 (t, J=7.9, 1H), 6.94 (d, J=7.2, 1H), 6.53 (d, J=8.6, 1H), 6.38 (d, J=4.1, 1H), 4.47-4.38 (m, 1H), 4.12 (dd, J=11.0, 4.3, 1H), 3.70-3.63 (m, 1H), 3.53 (t, J=10.0, 1H), 3.38 (dd, J=10.4, 4.6, 1H), 2.80-2.73 (m, 1H), 2.72-2.64 (m, 1H), 1.97-1.74 (m, 3H), 1.64-1.56 (m, 1H); MS (ESI+) m/z 273 (M+H)+.

According to the analysis of related databases, 189278-27-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ABBOTT LABORATORIES; US2011/294854; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 15862-37-0, 2,5-Dibromo-3-nitropyridine, 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 15862-37-0, blongs to pyridine-derivatives compound. Product Details of 15862-37-0

Step 1: Methyl 4-(5-bromo-3-nitropyridin-2-yl)benzoate To a mixture of 2,5-dibromo-3-nitropyridine (2.00 g, 7.09 mmol), (4-(methoxycarbonyl)phenyl)boronic acid (1.28 g, 7.09 mmol) Pd(dppf)C12 (0.36 g, 0.50 mmol) in THF (30 mL) was added tripotassium phosphate (3M in water) (7.09 mL, 21.3 mmol). The reaction mixture was purged with N2 (3x) and then stirred at 80 C for 3 h. The aqueous layer was separated. The organic layer dried with Na2SO4, filtered through a small plug of Celite washing with EtOAc and concentrated. The crude residue waspurified using ISCO silica gel chromatography (120 g column, gradient from 0% to 50% EtOAc/CH2C12) to give the title compound (1.64 g, 69%) as a white solid. Step 1: 5-Bromo-2-(2-fluoro-5-methanesulfonylphenyl)-3-nitropyridineFollowing procedures analogous to those described for methyl 4-(5-bromo-3-nitropyridin-2-yl)benzoate, 2-(2-fluoro-5 -methanesulfonylphenyl)-4,4,5 ,5 -tetramethyl1,3 ,2-dioxaborolane (500 mg, 1.66 mmol) was converted to the title compound (325 mg,52%). ?H NMR (500MHz, CDC13) oe 9.02 (d, J=2.0 Hz, 1H), 8.58 (d, J=2.0 Hz, 1H), 8.34(dd, J6.5, 2.4 Hz, 1H), 8.10 (ddd, J8.7, 4.7, 2.4 Hz, 1H), 7.34 (dd, J=9.4, 8.8 Hz, 1H),3.15 (s, 3H); LCMS (M+H) = 375; HPLC RT = 1.977 mm (Column: Chromolith ODS S54.6 x 50 mm; Mobile Phase A: 10:90 MeOH:water with 0.1% TFA; Mobile Phase B:90:10 MeOH:water with 0.1% TFA; Temperature: 40 C; Gradient: 0-100% B over 4 mm; Flow: 4 mL/min).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,15862-37-0, 2,5-Dibromo-3-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; NORRIS, Derek J.; DELUCCA, George V.; GAVAI, Ashvinikumar V.; QUESNELLE, Claude A.; GILL, Patrice; O’MALLEY, Daniel; VACCARO, Wayne; LEE, Francis Y.; DEBENEDETTO, Mikkel V.; DEGNAN, Andrew P.; FANG, Haiquan; HILL, Matthew D.; HUANG, Hong; SCHMITZ, William D.; STARRETT, JR, John E.; HAN, Wen-Ching; TOKARSKI, John S.; MANDAL, Sunil Kumar; WO2015/100282; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 7153-08-4, 3,5-Diiodopyridin-4-ol, 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, Safety of 3,5-Diiodopyridin-4-ol, blongs to pyridine-derivatives compound. Safety of 3,5-Diiodopyridin-4-ol

Example 405 N-[5-{7-(4-tert-Butylphenyl)furo[3,2-c]pyridin-2-yl}pyridin-3-yl]acetamide Step 1: Synthesis of N-{5-(7-iodofuro[3,2-c]pyridin-2-yl)pyridin-3-yl}acetamide [0743] A solution prepared by dissolving 3,5-diiodopyridin-4-ol (5.0 mmol), N-(5-ethynylpyridin-3-yl)acetamide (6.0 mmol) and copper(II) oxide (3.5 mmol) in anhydrous pyridine (30 ml) was stirred under reflux for 6 hours. The reaction mixture was cooled to room temperature, filtered through Celite, and concentrated under reduced pressure to yield brown oil. The residue was diluted with ethyl acetate, washed with aqueous ammonia, water and brine, in sequence, which was then dried over anhydrous magnesium sulfate and filtered. After the filtrate was concentrated, the residue thus obtained was purified by silica gel column chromatography (n-hexane/ethyl acetate=10/1, v/v) to obtain the title compound as light brown oil (yield: 49%).

The synthetic route of 7153-08-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; YUHAN CORPORATION; Seo, Hyoung Sig; Kim, Tae Kyun; Lee, Hyun Joo; Kim, Dong Hoon; Lee, Gyu Jin; Park, Jun Chul; Gal, Ji Yeong; Kim, Tae-hoon; Hyun, Kwan Hoon; Ahn, Kyoung Kyu; Park, Kaapjoo; Nam, Su Youn; Lee, Ge Hyeong; Lim, Hee Jong; US2015/191478; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem