Category: pyridine-derivatives

Adding a certain compound to certain chemical reactions, such as: 129432-25-3, 2,6-Dichloro-4-methylpyridin-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, 129432-25-3, blongs to pyridine-derivatives compound. SDS of cas: 129432-25-3

To a mixture of 2,6-dichloro-4-methylpyridin-3-amine (0.500 g, 2.82 mmol) and potassium thiocyanate (0.823 g, 8.47 mmol) in ethanol (7.5 mL) at rt was added concentrated hydrochloric acid (10.04 mL, 330 mmol) dropwise. The mixture was heated at 100 C for 44 h. Additional potassium thiocyanate (0.823 g, 8.47 mmol) was added and the mixture was heated at 100 C for additional 31 h. The reaction mixture was concentrated under vacuum to dryness. To the residue was added 1 N NaOH solution (10 mL), followed by solid K2CO3, until the mixture became basic (pH = 9-10). The mixture was extracted with dichloromethane (4 x 40 mL). The combined extracts were dried over anhydrous Na2S04, filtered, and concentrated under vacuum. The residue was purified by flash chromatograph (80 g silica gel, solid loading, 0-6% methanol/dichloromethane) to provide 5-chloro-7-methylthiazolo[5,4-b]pyridin-2-amine (0.331 g, 1.658 mmol, 58.7 % yield) as a tan solid. MS (ESI) m/z: 199.9 [M+H]+; NMR (500 MHz, DMSO-de) delta 7.90 (s, 2H), 7.22 (s, 1H), 2.41 (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,129432-25-3, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; FENG, Jianxin; LIU, Chunjian; HUANG, Yanting; (130 pag.)WO2019/89665; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 121643-44-5, 2-Methoxy-3-(trifluoromethyl)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, 121643-44-5, blongs to pyridine-derivatives compound. COA of Formula: C7H6F3NO

Intermediate 1 5-Bromo-2-methoxy-3-trifluoromethyl-pyridine To 2-methoxy-3-(trifluoromethyl)pyridine (20.0 g, 113.0 mmol) and 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione (43.6 g, 152.0 mmol) was added TFA (80 mL) and the resulting mixture stirred at rt for 18 h under argon. The TFA was removed in vacuo (50 mbar, 45 C.) and the residue suspended in tert-butyl methyl ether (200 mL). The resulting colourless solid was removed by filtration and washed with tert-butyl methyl ether (50 mL). The filtrate was concentrated in vacuo and suspended in EtOAc (50 mL) The insoluble colourless solid was removed by filtration and washed with EtOAc (50 mL). The filtrate was concentrated in vacuo, diluted with heptane/tert-butyl methyl ether (5/1, 20 mL) and the insoluble colourless solid was removed by filtration. The filtrate was purified by column chromatography on silica gel with heptane/EtOAc, 100/0 to 90/10. The crude product was filtered through a plug of NaHCO3 (20 g) and the filtrate evaporated in vacuo to give a golden oil (27.9 g). The oil was dissolved in heptanes (20 mL) and purified by filtered through a plug of silica gel (80 g), eluting with heptane to give 5-bromo-2-methoxy-3-(trifluoromethyl)pyridine as a colourless oil (22.5 g, 74% yield). 1H-NMR (400 MHz, DMSO-d6, 298 K): delta ppm 4.03 (s, 3H) 7.95 (d, 1H) 8.4 (d, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,121643-44-5, its application will become more common.

Reference:
Patent; NOVARTIS AG; COOKE, Nigel Graham; FERNANDES GOMES DOS SANTOS, Paulo Antonio; FURET, Pascal; HEBACH, Christina; HOGENAUER, Klemens; HOLLINGWORTH, Gregory; KALIS, Christoph; LEWIS, Ian; SMITH, Alexander Baxter; SOLDERMANN, Nicolas; STAUFFER, Frederic; STRANG, Ross; STOWASSER, Frank; TUFFILLI, Nicola; VON MATT, Anette; WOLF, Romain; ZECRI, Frederic; US2015/342951; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1042141-37-6, 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.1042141-37-6, name is Methyl 2-bromoimidazo[1,2-a]pyridine-6-carboxylate, molecular formula is C9H7BrN2O2, molecular weight is 255.07, as common compound, the synthetic route is as follows.

A mixture of methyl S-bromo-lJ-diazabicyclo^.S.Ojnona^^ojS-tetraene-S-carboxylate (0.65 mmol, 165 mg), tert-but5d N-methyl-N-[5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)pyridin-2-yl]carbamate (0.98 mmol, 312 mg), Pd(dprhof)Cl2*DCM (65 mumol, 53mg) and cesium carbonate (1.95 mmol, 656 mg) in DMF (5 mL) was heated at 80 CC under an argon atmosphere for 1 h. The reaction mixture was filtered and the solvent was evaporated in vacuo. The residue was purified by silica gel chromatography (EtOAc / hep) to give 150 mg of methyl 2-[6-[methyl-[(2-methylpropan- 2-yl)oxycarbonyl]amino]pyridin-3-yl]imidazo[2,l-fJpyridine-6-carboxylate as a yellow solid. MS m/z (M+H) 383

The chemical industry reduces the impact on the environment during synthesis 1042141-37-6, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ASTRAZENECA AB; WO2008/91195; (2008); A1;,
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. 5444-01-9, name is 4-Methylnicotinonitrile, the common compound, a new synthetic route is introduced below. Recommanded Product: 4-Methylnicotinonitrile

Preparation of Intermediate methyl 2-(3-cyanopyridin-4-yl)acetate (I-65a) 1M LiHMDS (45 mL, 44.794 mmol) was added to a solution of 4-methylnicotinonitrile (2.52 g, 21.33 mmol) in THF (15 mL) at -78 C. and the resulting reaction mass was stirred at -78 C. for 1 hour. This was followed by the addition of dimethyl carbonate (1.98 mL, 23.464 mmol) and stirred the resulting reaction mass at -78 C. for 1 hour and further at 0 C. for 2 hours. The reaction was monitored by TLC (30% ethyl acetate in hexane). The reaction mass was quenched with saturated NH4Cl solution and extracted using ethyl acetate. The organic layer was washed with water, brine solution, dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford the crude product. Purification by column chromatography on silica gel (25% ethyl acetate in hexane) afforded 530 mg of the product (14.10% yield). 1H NMR (300 MHz, CDCl3): delta 8.9 (s, 1H), 8.79 (d, 1H), 7.4 (d, 1H), 3.9 (s, 2H), 3.79 (s, 3H)

The synthetic route of 5444-01-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; Bock, Mark Gary; Gaul, Christoph; Gummadi, Venkateshwar Rao; Moebitz, Henrik; Sengupta, Saumitra; US2014/45872; (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. 29241-60-9, name is 5-Bromo-2-chloro-3-methylpyridine. A new synthetic method of this compound is introduced below., HPLC of Formula: C6H5BrClN

To a solution of 5-bromo-2-chloro-3-methylpyridine (300 g, 1.45 mol) in MeOH (3 L) was added freshly prepared sodium methoxide (156 g, 2.9 mol), and the reaction mixture was heated to reflux and stirred overnight. The reaction mixture was quenched with acetic acid (600 mL) and concentrated under reduced pressure. The crude mixture was diluted with ethyl acetate (3 L) and washed with water (3 L). The aqueous layer was extracted with ethyl acetate (3 L) and the combined organic layers were washed with brine (3 L), dried over anhydrous MgSCL and evaporated under reduced pressure to provide crude 5-bromo-2-methoxy-3-methylpyridine (220 g, 75%). l NMR (300 MHz, CDCl3) d (s, 1 H), 7.47 (s, 1 H), 3.93 (s, 3 H), 2.05 (s, 3 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, 29241-60-9, 5-Bromo-2-chloro-3-methylpyridine.

Reference:
Patent; GENENTECH, INC.; F. HOFFMANN-LA ROCHE AG; CUNNINGHAM, Christian; BEROZA, Paul Powell; CRAWFORD, James John; LEE, Wendy; RENE, Olivier; ZBIEG, Jason Robert; LIAO, Jiangpeng; WANG, Tao; YU, Chen; (208 pag.)WO2020/51099; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 179687-79-7, Adding some certain compound to certain chemical reactions, such as: 179687-79-7, name is 2-((2-Chloro-4-nitrophenoxy)methyl)pyridine,molecular formula is C12H9ClN2O3, 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 179687-79-7.

2-(2-CHLORO-4-NITRO-PHENOXYMETHYL)-PYRIDINE (2.4 g, 9.07 mmol) is suspended in MeOH (30 ML) and treated wet 5% Pt/C (Degussa type, ALDRICH, 0. 8 g). The flask is flushed with hydrogen gas from a balloon and the reaction mixture is stirred under hydrogen atmosphere until reaction is complete by TLC (ca 2 hours). The reaction mixture is filtered through a Celite plug and the solvent is removed under reduced pressure. The crude product is redissolved in DCM, dried (MGS04) and concentrated to yield 1.7 g (7.23 mmol, 80%) of the desired product.

According to the analysis of related databases, 179687-79-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARRAY BIOPHARMA, INC.; WO2004/46101; (2004); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 60154-05-4, 5-Iodo-1-methylpyridin-2(1H)-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, HPLC of Formula: C6H6INO, blongs to pyridine-derivatives compound. HPLC of Formula: C6H6INO

General procedure: A mixture of potassium fluoride (0.15g, 2.6mmol) and copper iodide (I) (0.50g, 2.6mmol) was heated under reduced pressure until a greenish color appeared, and after cooling to rt, an iodo compound (1.0mmol) in DMF/HMPA (2.5mL each) and trimethyl(trifluoromethyl)silane (0.38mL, 2.6mmol) were added to this flask successively. The mixture was stirred for the specified time and at the indicated temperature (see Table 2). After quenching with satd aqueous ammonium chloride, usual workup and purification by silica gel chromatography yielded the trifluoromethylated product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,60154-05-4, 5-Iodo-1-methylpyridin-2(1H)-one, and friends who are interested can also refer to it.

Reference:
Article; Kawasaki-Takasuka, Tomoko; Yamazaki, Takashi; Tetrahedron; vol. 71; 38; (2015); p. 6824 – 6831;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 717843-56-6, 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. 717843-56-6, name is 3-Bromo-2-methoxy-5-methylpyridine, molecular formula is C7H8BrNO, 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.

Step AM2: 3-Bromo-5-bromomethyl-2-methoxy-pyridine To a solution of 3-bromo-2-methoxy-5-methyl-pyridine (Step AM3) (3.0 g, 14.7 mmol), was added NBS (3.1 g, 17.6 mmol) and AIBN (121 mg, 0.7 mmol) and the mixture was stirred at 80 C. for 1 h. H2O and CH2Cl2 were added and the phases were separated. The organic layer was dried (MgSO4), filtered and concentrated. The crude product was purified by silica gel column chromatography (heptane/EtOAc, 95:5?0:100). tR: 1.10 min (LC-MS 1).

According to the analysis of related databases, 717843-56-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; Cotesta, Simona; Furet, Pascal; Guagnano, Vito; Holzer, Philipp; Kallen, Joerg; Mah, Robert; Masuya, Keiichi; Schlapbach, Achim; Stutz, Stefan; Vaupel, Andrea; US2013/317024; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 143803-93-4 ,Some common heterocyclic compound, 143803-93-4, molecular formula is C9H8N2O2, 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.

General procedure: These were made by decarboxylation/Vilsmeier or hydrolysis/reduction/reoxidation as detailed below, unless otherwise stated.Decarboxylation was carried out by refluxing a solution of the ester (1 equiv) in 40% aqueous H2SO4 (3 mL) for 18 h. The solution was then cooled in ice and neutralised to pH 7 with 6 M NaOH, then extracted twice with CH2Cl2. The combined extracts were dried (Na2SO4) and the solvent removed in vacuo to leave the decarboxylated material. The pyrazolo[1,5-a]pyridine was then reacted under Vilsmeier conditions in dry DMF (2 mL) with POCl3 (3 equiv) at 0 C under an atmosphere of N2. The reaction mixture was then warmed to room temperature and stirred for 2 h. The solution was poured onto ice, basified to pH 10 with 1 M NaOH, stirred for 1 h then extracted twice with CH2Cl2. The combined extracts were washed twice with water, dried (Na2SO4) and the solvent removed in vacuo to leave the aldehyde.Alternatively, the ester was hydrolysed by refluxing a solution of the ester (1 equiv) in 1 M NaOH (3 equiv) and EtOH (5 mL) for 6 h. The EtOH was removed in vacuo, and then the aqueous residue acidified to pH 1 with 1 M HCl. The precipitated carboxylic acid was filtered off, washed with water and dried. The carboxylic acid was reduced by adding CDI (1.5 equiv) to a suspension of carboxylic acid (1 equiv) in dry THF (10 mL) under an atmosphere of N2. After stirring for 18 h, the resulting solution was added dropwise to a solution of NaBH4 (5 equiv) in H2O (10 mL) and stirred for 30 min. The reaction was then quenched by the addition of 1 M HCl and stirred for a further 30 min. The solution was neutralised with saturated aqueous NaHCO3 and extracted twice with CH2Cl2. The combined organic layers were dried (Na2SO4) and the solvent removed in vacuo. Chromatography (eluting with a hexanes: EtOAc gradient) gave the alcohol. Reoxidation was carried out by stirring a suspension of the pyrazolo[1,5-a]pyridine-3-methanol (1 equiv) and MnO2 (10 equiv) in CH2Cl2 (2 mL) at room temperature for 4 days. The reaction mixture was then filtered through celite, washed with CH2Cl2, and the solvent removed from the filtrate in vacuo to leave the aldehyde.

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. 143803-93-4, 4-Methylpyrazolo[1,5-a]pyridine-3-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kendall, Jackie D.; O’Connor, Patrick D.; Marshall, Andrew J.; Frederick, Raphael; Marshall, Elaine S.; Lill, Claire L.; Lee, Woo-Jeong; Kolekar, Sharada; Chao, Mindy; Malik, Alisha; Yu, Shuqiao; Chaussade, Claire; Buchanan, Christina; Rewcastle, Gordon W.; Baguley, Bruce C.; Flanagan, Jack U.; Jamieson, Stephen M.F.; Denny, William A.; Shepherd, Peter R.; Bioorganic and Medicinal Chemistry; vol. 20; 1; (2012); p. 69 – 85;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 823-61-0 ,Some common heterocyclic compound, 823-61-0, molecular formula is C7H10N2, 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.

To a solutionof 26-S3 (170 mg, 0.44 mmol) and 6-methylpyridin-2-amine (90 mg, 0.48 mmol) in DCE (5 mL) were added DIPEA (0.29 mL, 1.76 mmol) and EEDQ (217 mg, 0.88 mmol). The reaction mixture was stirred at 90 C overnight and concentrated under high vacuum. The remaining residue was purified by column chromatography on silica gel (eluted with PE/EtOAc = 4:1) to afford 26-S4(103 mg, 41% yield) as a yellow solid. LC/MS (ESI) m/z: 555/557 (M+H)t

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,823-61-0, its application will become more common.

Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason, Allan; PHADKE, Avinash, S.; DESHPANDE, Milind; AGARWAL, Atul; CHEN, Dawei; GADHACHANDA, Venkat, Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; BARRISH, Joel, Charles; GREENLEE, William; EASTMAN, Kyle, J.; (0 pag.)WO2018/160889; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem