Month: April 2022

Application of 54221-93-1, 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. 54221-93-1, name is 2,6-Dimethylisonicotinic acid. A new synthetic method of this compound is introduced below.

A mixture of 2 g of 2,6-dimethylisonicotinic acid (2) (unpurified), 100 ml of methanol and 1 ml of 98% sulfuric acid is refluxed for 24 hours. After cooling, the reaction medium is neutralized with saturated NaHCO3 solution and then extracted five times with 60 ml of CHCl3. The combined chloroform phases are then dried over Na2SO4 and then concentrated. The resulting solid is then extracted four times with 50 ml of ether, after which the ether phase is concentrated. Chromatography on alumina [gradient: cyclohexane/CH2Cl2 (50/50) to pure CH2Cl2] of the white residue obtained gives 1 g of 4-methyl-2,6-dimethyl isonicotinate (3). [0141] m.p.: 45-47 C. [0142] TLC: Rf: 0.3 [SiO2/CH2Cl2-MeOH (97/3)][0143] HPLC: Tr: 2.4 [0144] UV: CHCl3: 290.6 nm (3650) [0145] NMR: 1H CDCl3; internal reference TMS [0146] 2.59 (s, 6H, CH3); 3.93 (s, 3H, CO2CH3); 7.51 (s, 2H, Py) [0147] 13C CDCl3; internal reference 77.0 ppm [0148] 24.5 (CH3); 52.5 (OCH3); 119.5 (Ct); 137.9, 158.9 (Cq); [0149] 166.1 (CO). [0150] MS (EI): 165 (M+, 24); 134 (M+-OCH3, 13); 106 (M+-CO2Me)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,54221-93-1, its application will become more common.

Reference:
Patent; Autiero, Herve; Bazin, Herve; Mathis, Gerard; US2004/92726; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 120739-77-7, 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. 120739-77-7, name is N-((6-Chloropyridin-3-yl)methyl)ethanamine. A new synthetic method of this compound is introduced below.

EXAMPLE 12 A solution of 2.4 g (0.014 mol) of N-(6-chloro-3-pyridyl)methyl-N-ethylamine, 1.4 g (0.014 mol) of triethylamine in 5 ml of acetonitrile was dropwise added to a solution of 2.0 g (0.014 mol) of 1,1-dichloro-2-nitroethylene in 35 ml of acetonitrile at 3-5 C. with stirring. After stirring for 30 minutes, 4.4 g (0.057 mol) of methylamine (40% methanol solution) were added to the reaction mixture and stirred for 30 minutes. The reaction mixture was filtered, and the filtrate was concentrated and purified by a silica gel column chromatography (chloroform/ethanol=7/1) to afford 2.9 g (76.5%) of 1-[N-(6-chloro-3-pyridyl)methyl-N-ethyl]amino-1-methylamino-2-nitroethylene as pale yellowish crystals.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,120739-77-7, its application will become more common.

Reference:
Patent; Takeda Chemical Industries, Ltd.; US5364989; (1994); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 17570-98-8, 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.17570-98-8, name is 2-(Bromoacetyl)pyridine hydrobromide, molecular formula is C7H7Br2NO, molecular weight is 280.95, as common compound, the synthetic route is as follows.

EXAMPLE 1a; [(methylethyl)sulfonyl](trans-4-{[(4-(2-pyridyl)(1,3-thiazol-2-yl))amino]methyl}cyclohexyl)amine; N-({[(trans-4-{[(methylethyl)sulfonyl]amino}cyclohexyl)methyl]amino}thioxomethyl)amide (0.60 g, 2.0 mmol) was added to a stirred solution of 2-bromo-1-(2-pyridyl)ethan-1-one hydrobromide (0.57 g, 2.0 mmol) in EtOH (20 mL) at rt followed by the addition of DIEA (1.05 mL, 6.0 mmol). The reaction mixture was heated at reflux for 4 h, cooled to rt, and concentrated in vacuo. The resultant residue was re-dissolved in CHCl3 and washed successively with aqueous citric acid, water and brine. The organic layer was dried over Na2SO4 and concentrated in vacuo. The crude product was purified by silica gel column chromatography (60% EtOAc in Hexanes) to afford the desired product as a tan colored solid (0.56 g, 69%). 1H NMR (CDCl3) delta 8.58 (d, 1H, J=4.8 Hz), 7.89 (dt, 1H, J=7.6 and 1.2 Hz), 7.71 (td, 1H, J=7.8 and 2.0 Hz), 7.17 (td. 1H, J=4.8 and 1.2 Hz), 5.25 (br s, 1H), 3.85 (d, 1H, J=8.4 Hz), 3.25 (br m, 1H), 3.18 (t, 2H, J=6.4 Hz), 2.14 (dt, 2H, J=12.0 and 1.2 Hz), 2.19 (br, d, 2H, J=12.8 Hz), 1.62 (br m, 3H), 1.38 (d, 6H, J=6.8 Hz), 1.25 (dq, 2H, J=12.8 and 1.6 Hz). LC-MS m/e: 395 (M+H)+; tR=2.14 min (Method-A).

Statistics shows that 17570-98-8 is playing an increasingly important role. we look forward to future research findings about 2-(Bromoacetyl)pyridine hydrobromide.

Reference:
Patent; Jubian, Vrej; Packiarajan, Mathivanan; Jimenez, Hermogenes; Reinhard, Emily; US2006/293341; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 83766-88-5, name is 2-(tert-Butoxy)pyridine. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C9H13NO

Carboxylic acid (0.2 g, 1.64 mmol), tert-butoxypyridine (0.33 g, 2.21 mmol) and boron trifluoride diethyl etherate (0.31 g, 2.21 mmol) in dry PhCH3 (2 mL) were added to a 20-ml vial. The reaction mixture was then allowed to stir at room temperature for 30 min before quenching with anhydrous NaHCO3. The reaction mixture was diluted with ethyl acetate (30 mL), then washed with water (20 mL), followed by brine (20 mL). The organic layer was dried over anhydrous sodium sulfate and carefully concentrated under reduced pressure. The resulting residue was then purified by flash column chromatography on silica gel with 0:4 to 1:4 dichloromethane/hexane as eluent to yield the desired product 5a as a colorless oil.

With the rapid development of chemical substances, we look forward to future research findings about 83766-88-5.

Reference:
Article; La, Minh Thanh; Kim, Hee-Kwon; Tetrahedron; vol. 74; 27; (2018); p. 3748 – 3754;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 55876-82-9, Ethyl 5-methylpicolinate, 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, 55876-82-9, blongs to pyridine-derivatives compound. SDS of cas: 55876-82-9

Synthesis Example 2 2-Carboxy-5-methylpyridinium chloride STR25 78.1 g of the crude product of the ethyl 5-methylpyridine-2-carboxylate obtained in Synthesis Example 1 was dissolved in 200 ml of 6N-hydrochloric acid, followed by heating under reflux for 16 hours. The reaction solution was concentrated in a reduced pressure. Then, acetonitrile was added to the residue, and the white crystal thus precipitated was recovered by filtration, washed with acetonitrile and dried at 90 C. to give 26.3 g of the title compound. Yield 37%. 1H-NMR (400 MHz, CDCl3) delta; 8.51 (1H, m), 8.37 (1H, m), 8.21 (1H, d, J=8.0 Hz), 2.42 (3H, s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,55876-82-9, its application will become more common.

Reference:
Patent; Eisai Co., Ltd.; US5789403; (1998); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 2369-19-9 , The common heterocyclic compound, 2369-19-9, name is 2-Fluoro-5-methylpyridine, molecular formula is C6H6FN, 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 38A 2-fluoro-4-iodo-5-methylpyridine A solution of dilsopropylamine (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.

The synthetic route of 2369-19-9 has been constantly updated, and we look forward to future research findings.

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; US2003/87940; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 38186-86-6 ,Some common heterocyclic compound, 38186-86-6, molecular formula is C6H3ClFNO2, 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 19 2-Chloro-3-fluoro-5-trifluoromethylpyridine A steel bomb was charged with 6-chloro-5-fluoronicotinic acid (5.4 g, 0.03 m), SF4 (32.4 g) and HF (5.6 ml). The mixture was heated at 120 for eight hours. After cooling to 25, the bomb was vented and the contents poured onto ice. The solution was neutralized with saturated Na2 CO3 solution and extracted with CH2 Cl2. The organic layer was dried over Na2 SO4, filtered and the solvent distilled off on a steam bath. The residue was distilled at 115 (760 mm) to yield 1.4 g (23% yield) of 2-chloro-3-fluoro-5-trifluoromethylpyridine.

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. 38186-86-6, 6-Chloro-5-fluoronicotinic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Merck & Co., Inc.; US4279913; (1981); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1211532-15-8 , The common heterocyclic compound, 1211532-15-8, name is 6-Methoxy-5-(trifluoromethyl)nicotinic acid, molecular formula is C8H6F3NO3, 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.

Preparation Example 4 To a mixture of 6-methoxy-5-(trifluoromethyl)nicotinic acid (7.8 g) and dichloromethane (80 mL) were added N,O-dimethylhydroxylamine hydrochloride (4.3 g), WSCD.HCl (9.5 g), and N,N-diisopropylethylamine (30 mL) under ice-cooling. The reaction mixture was stirred at room temperature for 17 hours. The reaction mixture was concentrated under reduced pressure, and to the residue were added ethyl acetate and water, followed by stirring for 30 minutes. The organic layer was separated, the aqueous layer was extracted with ethyl acetate, and the organic layer was combined, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain N,6-dimethoxy-N-methyl-5-(trifluoromethyl)nicotinamide (5.0 g) as an oil.

The synthetic route of 1211532-15-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Astellas Pharma Inc.; TAKAHASHI, Taisuke; KOIKE, Takanori; NEGORO, Kenji; TANAKA, Hiroaki; MAEDA, Jun; YOKOYAMA, Kazuhiro; TAKAMATSU, Hajime; (146 pag.)EP3153511; (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.113118-82-4, name is 5-Chloronicotinaldehyde, molecular formula is C6H4ClNO, molecular weight is 141.5551, as common compound, the synthetic route is as follows.COA of Formula: C6H4ClNO

General procedure: Oleanolic acid analogues 4e29 were obtained from Scheme 1.Firstly, oleanolic acid (0.66 mmol) and selectfluor (1-chloromethy l-4-fluoro-1, 4-diazoniabicyclo [2.2.2] octane bis (tetrafluoroborate))(1.98 mmol) were dissolved in the mixed solution of anhydrousdioxane (4 mL) and nitromethane (6 mL), and stirred at 80 C for4 h. Then the reaction mixture was concentrated under reducedpressure, extracted with ethyl acetate and deionized water, filteredand dried with anhydrous magnesium sulfate. Next, the crudeproduct was purified on a silica gel column with petroleum ether/ethyl acetate (v/v 5:1) as the eluent to obtain the intermediate OA-F.Secondly, OA-F (0.51 mmol) was added into 75 mL of acetone andstirred at 0 C until it was completely dissolved. Then the Jonesreagent (0.5 mL) was slowly added into the solution and stirred for5 min. After pretreatment similar with OA-F, the crude product waspurified via dichloromethane/petroleum ether (v/v 2:1/3:1) asthe eluent on silica gel column to produce another intermediateOA-F-01. Finally, OA-F-01 (0.44 mmol) and potassium hydroxide(0.88 mmol) were dissolved in the mixed solution of dichloromethane(10 mL) and ethanol (10 mL) followed by adding aldehyde(0.88 mmol) and stirring at room temperature for 12 h. After pretreatmentsimilar with OA-F and OA-F-01, petroleum ether/dichloromethane or ethyl acetate were used as the eluent to purifythe crude product for gaining the analogues 4-29.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,113118-82-4, 5-Chloronicotinaldehyde, and friends who are interested can also refer to it.

Reference:
Article; Zhong, Ying-Ying; Chen, Hui-Sheng; Wu, Pan-Pan; Zhang, Bing-Jie; Yang, Yang; Zhu, Qiu-Yan; Zhang, Chun-Guo; Zhao, Su-Qing; European Journal of Medicinal Chemistry; vol. 164; (2019); p. 706 – 716;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 83766-88-5, 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. 83766-88-5, name is 2-(tert-Butoxy)pyridine. A new synthetic method of this compound is introduced below.

Carboxylic acid (0.2 g, 1.64 mmol), tert-butoxypyridine (0.33 g, 2.21 mmol) and boron trifluoride diethyl etherate (0.31 g, 2.21 mmol) in dry PhCH3 (2 mL) were added to a 20-ml vial. The reaction mixture was then allowed to stir at room temperature for 30 min before quenching with anhydrous NaHCO3. The reaction mixture was diluted with ethyl acetate (30 mL), then washed with water (20 mL), followed by brine (20 mL). The organic layer was dried over anhydrous sodium sulfate and carefully concentrated under reduced pressure. The resulting residue was then purified by flash column chromatography on silica gel with 0:4 to 1:4 dichloromethane/hexane as eluent to yield the desired product 5a as a colorless oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,83766-88-5, its application will become more common.

Reference:
Article; La, Minh Thanh; Kim, Hee-Kwon; Tetrahedron; vol. 74; 27; (2018); p. 3748 – 3754;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem