Category: pyridine-derivatives

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. 381247-99-0, name is Methyl 5-bromo-6-hydroxynicotinate. A new synthetic method of this compound is introduced below., SDS of cas: 381247-99-0

Step 1: Methyl 5-bromo-l-methyl–oxo-1,6-dihvdropyridine-3-carboxvlate. A mixture of methyl 5-bromo-6-oxo-l,6-dihydropyridine-3-caboxylate (1.5 g, 6.5 mmol)and potassium carbonate (0.99 g, 7.15 mmol) in DMF (25 mL) was stirred at room temperature for 15 min followed by the addition of methyl iodide (0.42 mL, 6.83 mmol). The resulting suspension was stirred at room temperature for 17 h. The mixture was partitioned between ethylacetate and water. The organic phase was separated and the aqueous phase was extracted with ethylacetate. The organic extracts were combined, washed with brine, dried over MgSO4 and concentrated to afford the title compound as a light yellow solid. MS m/z: 246(M+1).

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, 381247-99-0, Methyl 5-bromo-6-hydroxynicotinate.

Reference:
Patent; AMGEN INC.; WO2007/62007; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 83640-36-2, 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 83640-36-2, name is 6-(Chloromethyl)nicotinonitrile. This compound has unique chemical properties. The synthetic route is as follows.

A. Preparation of 6-((8-bromo-7-(4-chlorophenyl)-3-oxo-[1,2,4]triazolo[4,3-a]pyridin-2(3H)-yl)methyl)nicotinonitrile To a stirred mixture of 8-bromo-7-(4-chlorophenyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one (1.07 g, 3.31 mmol) in DMF (15 mL) at room temperature under argon was added K2CO3 (0.91 g, 6.62 mmol) and 6-(chloromethyl)nicotinonitrile (0.63 g, 4.14 mmol). The mixture was then heated to 60 C. for 7 h, after which HPLC indicated complete reaction. The mixture was cooled to room temperature, diluted with water (100 mL), and stirred for 30 min. Solid was collected by filtration and washed with water (10 mL*5), then methanol (3 mL*3), and finally dried under vacuum. The title compound (0.98 g) was obtained as a tan solid. HPLC/MS: retention time=3.4 min, [M+H]+=442.

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 83640-36-2, 6-(Chloromethyl)nicotinonitrile.

Reference:
Patent; Sun, Chongqing; Sher, Philip M.; Wu, Gang; Ewing, William R.; Huang, Yanting; Lee, Taekyu; Murugesan, Natesan; Sulsky, Richard B.; US2007/4772; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1070892-04-4, 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 1070892-04-4, name is 5-Bromo-2-(trifluoromethyl)isonicotinonitrile. This compound has unique chemical properties. The synthetic route is as follows.

To a mixture of delta-bromo^-trifluoromethyl-isonicotinonitrile 1-1 (2.51 g, 10 mmol) in dioxane (3.3 mL) and water (3.3 ml_), were added 2-chloro-4- methoxyphenylboronic acid (2.3 g, 12.5 mmol) and Na2CO3 (6.3 g). The mixture was purged with nitrogen gas for 10 min, then Pd(PPh3)4 (1.2 g, 1.0 mmol) was added. The mixture was stirred in a sealed vessel at 85 0C for 6 hrs, then extracted by ethyl acetate. The organic layer was washed with water, dried over MgSO4. Concentration and purification by silica gel column chromatography eluting with hexane/ethyl acetate (10/1 ) yielded 5-(2-chloro-4-methoxy-phenyl)-2-trifluoromethylisonicotinonitrile (1.31 g). tR = 2.96 min (method 1).

According to the analysis of related databases, 1070892-04-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NEUROCRINE BIOSCIENCES, INC.; WO2008/124614; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 89978-52-9, 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 89978-52-9, name is Ethyl 2-bromoisonicotinate. This compound has unique chemical properties. The synthetic route is as follows.

4-cyano-2-naphthaleneboronic acid (0.10 g), 2-bromoisonicotinic acid ethyl ester (0.12 g) and cesium fluoride (0.09 g) in dimethoxyethane (6 mL) was added tetrakis (triphenylphosphine) palladium (0.06 g), and the mixture was stirred at 150C for 40 minutes using microwave reactor (Biotage). The reaction mixture was filtered through a Celite pad, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=100/0-66/34) to give 2-(4-cyanonaphthalene-2-yl) isonicotinic acid ethyl ester (0.14 g). To a solution of this compound (0.14 g) in a mixed solvent of tetrahydrofuran (4 mL), ethanol (1 mL) and water (1 mL) was added lithium hydroxide monohydrate (0.060 g), and the mixture was stirred at room temperature overnight. To the reaction mixture was added acetic acid (0.27 mL). The precipitated solid was collected by filtration, and washed with water and n-hexane. The solid was dried under reduced pressure to give the title compound (0.098g).

According to the analysis of related databases, 89978-52-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Kissei Pharmaceutical Co., Ltd.; SHIMIZU, Kazuo; IIZUKA, Masato; FUJIKURA, Hideki; TAKIGAWA, Yasushi; HIRATOCHI, Masahiro; EP2343279; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 69045-83-6 ,Some common heterocyclic compound, 69045-83-6, molecular formula is C6H2Cl5N, 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.

EXAMPLE 7 This Example illustrates the preparation of 2,3-dichloro-5-trifluoromethylpyridine by fluorination of 2,3-dichloro-5-trichloromethylpyridine, using a fluorinating agent alternative to that of Example 6. 2,3-Dichloro-5-trichloromethylpyridine (35 g) was heated with anhydrous hydrogen fluoride (100 g) in an autoclave at 200 for 10 hours with stirring. The cooled reaction mixture was poured on to ice and neutralised with sodium hydroxide at 0. The mixture was extracted with methylene chloride (750 ml). The extracts were washed with water (500 ml), sodium carbonate solution (500 ml) and water (500 ml), dried, and evaporated. The remaining oil was distilled and the fraction of boiling point 77-83/25 Torr was collected and identified as the required pyridine derivative.

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. 69045-83-6, 2,3-Dichloro-5-(trichloromethyl)pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Imperial Chemical Industries Limited; US4317913; (1982); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 2369-19-9, 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. 2369-19-9, name is 2-Fluoro-5-methylpyridine, molecular formula is C6H6FN, 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 38A 2-fluoro-4-iodo-5-methylpyridine A solution of diisopropylamine (7.0 mL, 50.0 mmol) in THF (100 mL) at -78 C. was treated with 2.5M n-butyllithium in hexanes (20 mL, 50.0 mmol), stirred for 15 minutes, treated dropwise with a solution of 2-fluoro-5-methylpyridine (5.55 g, 50.0 mmol) in THF (20.0 mL), stirred for 4 hours, treated slowly with a solution of iodine (12.7 g. 50.0 mmol) in THF (50 mL), quenched with water, and extracted with diethyl ether. The combined extracts were washed sequentially with Na2S2O3, water, and brine, dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 6:1 hexanes/diethyl ether to provide 7.24 g (61%) of 2-fluoro-3-iodo-5-methylpyridine.

According to the analysis of related databases, 2369-19-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Claiborne, Akiyo K.; Gwaltney, II, Stephen L.; Hasvold, Lisa A.; Li, Qun; Li, Tongmei; Lin, Nan-Horng; Mantei, Robert A.; Rockway, Todd W.; Sham, Hing L.; Sullivan, Gerard M.; Tong, Yunsong; Wang, Gary; Wang, Le; Wang, Xilu; Wang, Wei-Bo; US2002/115640; (2002); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 184368-74-9, 1-tert-Butyl 4-methyl 5,6-dihydropyridine-1,4(2H)-dicarboxylate, 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, Recommanded Product: 184368-74-9, blongs to pyridine-derivatives compound. Recommanded Product: 184368-74-9

C. 1-boc-1,2,3,6-Tetrahydro-4-pyridinecarboxylic Acid To a stirred solution of methyl 1-Boc-1,2,3,6-tetrahydro-4-pyridinecarboxylate (2.22 g, 9.2 mmol) in methanol (10 mL) was added 1.0 N aqueous sodium hydroxide (25 mL). After stirring for 2 h, the solvent was removed in vacuo. The residue was partitioned between diethyl ether and water, and the layers were separated. The aqueous phase was acidified to pH 2.5 with concentrated hydrochloric acid and extracted with ethyl acetate. The organic extract was washed with saturated aqueous sodium chloride, dried (magnesium sulfate), filtered, and concentrated in vacuo to give 1.62 g (78%) of the title compound as a white solid. 1H-NMR; IS-MS, m/e 226.1 (m-1)-; Analysis for C11H17NO4: Calcd: C, 58.14; H, 7.54; N, 6.16; Found: C, 57.41; H, 7.48; N, 6.19.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,184368-74-9, 1-tert-Butyl 4-methyl 5,6-dihydropyridine-1,4(2H)-dicarboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Eli Lilly and Company; US6635657; (2003); B1;,
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. 851484-95-2, name is 2-Chloro-5-fluoronicotinaldehyde. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 2-Chloro-5-fluoronicotinaldehyde

2-chloro-5-fluoronicotinaldehyde (20 g, 125 mmol) was taken up in THF (150 ml) at 0 C. (R)-2-Methylpropane-2-sulfinamide (16.71 g, 138 mmol) was added followed by dropwise additionof titaniumtetraethanolate (22.88 ml, 150 mmol). The reaction mixture was stirred while warming to RT. After 3 hours the reaction mixture was cooled to 0 C, and 150m1 of brine was added and stirred for 20 minutes. The mixture was filtered through Celite. The aqueous layer was separated and discarded. The organic layer with dried over Na2SO4 and the solvent was removed to give(S ,Z)-N-((2-chloro-5-fluoropyridin-3 -yl)methylene)-2-methylpropane-2- sulfinamide (32 g, 122 mmol, 97 % yield), which was carried on without further purification. LCMS: 263 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, 851484-95-2, 2-Chloro-5-fluoronicotinaldehyde.

Reference:
Patent; BLUEPRINT MEDICINES CORPORATION; WENGLOWSKY, Steven, Mark; MIDUTURU, Chandrasekhar, V.; BIFULCO, Neil, Jr; KIM, Joseph, L.; (91 pag.)WO2017/87778; (2017); 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.685115-77-9, name is 1-(3,5-Dichloropyridin-4-yl)piperidine-4-carboxamide, molecular formula is C11H13Cl2N3O, molecular weight is 274.15, as common compound, the synthetic route is as follows.Computed Properties of C11H13Cl2N3O

To a suspension of 1-(3,5-dichloropyridin-4-yl)piperidine-4-carboxamide 23 (75 mg, 0.27 mmol), 1 ,5-dimethyl-4-pyrazole boronic acid pinacol ester (76 mg, 0.34 mmol) and tetrakis(triphenylphosphine)palladium(0) (16 mg, 5mol%) in acetonitrile (3 ml.) was added 0.5 M solution of sodium carbonate (0.77 ml_, 0.38 mmol). The mixture was heated to in a microwave reactor at 150 0C for 45 min. Once cooled the reaction was concentrated in vacuo and dry loaded onto silica. The crude product was purified by flash column chromatography on silica gel (CH2CI2, EtOH, 97:3-80:20, biotage 25+S) to furnish the title compound as a clear colourless oil (24 mg, 26%), LC-MS (ESI, 4 min) Rt 1.49 min, m/z 334 (100%, [M+H]+); m/z (ESI) Ci6H20N5OCI requires 333.1356, found [M+H]+ 333.1354.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,685115-77-9, 1-(3,5-Dichloropyridin-4-yl)piperidine-4-carboxamide, and friends who are interested can also refer to it.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; McDONALD, Edward; BLAGG, Julian; PICHOWICZ, Mark; CRUMPLER, Simon Ross; WO2010/41054; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1256810-26-0, Adding some certain compound to certain chemical reactions, such as: 1256810-26-0, name is 6-Bromo-3-methoxypicolinic acid,molecular formula is C7H6BrNO3, 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 1256810-26-0.

To a solution of (4-chlorophenyl)methanamine (610 mg, 4.31 mmol), 6-bromo-3- methoxypicolinic acid (1.0 g, 4.31 mmol) and triethylamine (1.31 g, 12.9 mmol) in DCM (10 mL) was added dropwise T3P (2.74 g, 8.61 mmol) at 0C. Five minutes later, TLC indicated the reaction was complete, and the mixture was suspended in water and extracted with DCM. The organic phase was washed with brine, dried over sodium sulfate and concentrated in vacuo to give the crude 6-bromo-N-(4-chlorobenzyl)-3-methoxypicolinamide (1.3 g, yield: 87%) without further purification. -NMR (DMSO-i, 400 MHz) delta 8.98 (t, J = 6.0 Hz, 1H), 7.69 (d, J = 8.8 Hz, 1H), 7.58 (d, J = 8.8 Hz, 1H), 7.39-7.43 (m, 2H), 7.33 (d, J = 8.4 Hz, 2H), 4.22 (d, J = 6.4 Hz, 2H), 3.84 (s, 3H). MS (M+H)+: 355 / 357.

According to the analysis of related databases, 1256810-26-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DAI, Xing; LIU, Hong; PALANI, Anandan; HE, Shuwen; NARGUND, Ravi; XIAO, Dong; ZORN, Nicolas; DANG, Qun; MCCOMAS, Casey, C.; PENG, Xuanjia; LI, Peng; SOLL, Richard; WO2014/209727; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem