Day: April 11, 2022

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

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. 87674-15-5, name is 1-(3-Fluoropyridin-4-yl)ethanol, the common compound, a new synthetic route is introduced below. Formula: C7H8FNO

a) 4-(l-Chloroethyl)-3-fluoropyridinel-(3-fluoropyridin-4-yl)ethanol (0.8 g, 5.7 mmol) was treated with thionyl chloride (5 mL) and the resulting mixture was heated to 80 C for 2 h. Water (10 mL) and sat. sodium bicarbonate (aq., 10 mL) was added. The product was extracted with DCM (three times). The combined organic extracts were washed with brine, dried over sodium sulphate and concentrated in vacuo. The crude product was purified by flash column chromatography (eluent heptane: ethyl acetate gradient) to yield 0.36 g (39% yield) of the title compound. 1H NMR (300 MHz, CDCl3) 8.45 (m, 2H), 7.50 (m, IH), 5.34 (q, IH), 1.83 (d, 3H).

The synthetic route of 87674-15-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; WO2008/39138; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 66909-38-4, 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. 66909-38-4, name is 6-Chloro-4-methylpyridin-3-amine, molecular formula is C6H7ClN2, 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.

6-Chloro-4-methylpyridin-3-amine (22.0 g, 154.9 mmol) was dissolved in DMF (150 mL) and treated with NIS (41.8 g, 185.9 mmol). The reaction mixture was stirred at rt overnight, then water (200 mL) was added, and the mixture was extracted with EtOAc (3×200 mL). The combined organics were concentrated in vacuo and the residue was subjected to silica gel flash chromatography eluting with Et2O-EtOAc to give 6-chloro-2-iodo-4-methylpyridin-3-amine. 1H NMR (DMSO-d6, 400 MHz): delta7.11 (s, 1H), 5.23 (s, 2H), 2.15 (s, 3H) ppm

According to the analysis of related databases, 66909-38-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Gilead Sciences, Inc.; Aktoudianakis, Evangelos; Chin, Gregory; Mackman, Richard L.; Metobo, Samuel E.; Mish, Michael R.; Pyun, Hyung-jung; Zablocki, Jeff; (175 pag.)US2016/289229; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 24207-22-5 ,Some common heterocyclic compound, 24207-22-5, molecular formula is C7H8BrNO, 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.

[0125] 2-Bromo-3-methoxy-6-methylpyridine (XXXXV) 760 mg (3.76 mmol) was dissolved in 15 ml of water, and to the resulting solution was added potassium permanganate (KMnO4) (1.49 g, 9.40mmol) and the mixture was heated at 80 C for 3 hrs. After TLC was conducted, pH was adjusted to 4 with 10% hydrochloric acid (HCl) and filtration was conducted with celite. The filtrate was extracted with 50 ml of ethylacetate (EA). The organic layer was treated with magnesium sulfate (MgSO4) and filtered, and the solution was concentrated to give the title compound as a white solid (665 mg, 2.87 mmol, 75 %) without purification. 1H NMR (400 MHz, DMSO-d6) delta 13.22 (s, OH), 8.05 (d, J = 8.0 Hz, 1H), 7.60 (d, J = 8.0 Hz, 1H), 4.02 (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,24207-22-5, its application will become more common.

Reference:
Patent; Beyondbio Inc.; MIN, Changhee; OH, Byungkyu; KIM, Yongeun; PARK, Changmin; (98 pag.)EP3255042; (2017); A2;,
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. 135450-23-6, name is 6-(Chloromethyl)-2-cyanopyridine, the common compound, a new synthetic route is introduced below. Recommanded Product: 135450-23-6

[00369] 6-((((tert-Butoxy)carbonyl)amino)methyl)picolinonitrile (P31): To a solution of commercially available chloride P30 (9.66 g, 63.3 mmol) in DMF (400 mL) at ambient temperature was treated with potassium phthalimide (11.7 g, 63.3 mmol). After stirring for 5 h, the mixture was concentrated under vacuum. The remaining mixture was taken up in H20 (200 mL) and was filtered to collect the solid. The solid was washed with H20 (100 mL) and THF (100 mL) to obtain the desired phthalimide derivative (11.5 g, 69%) and was moved forward without further purification. To a solution of the crude phthalimide derivative (5.84 g, 22.2 mmol) in THF/MeOH (200 mL, 1:1, v/v) at ambient temperature was treated with hydrazine monohydrate (1.18 mL, 24.4 mmol). After 2 h, 1.0 M HC1 (24.5 mL) was added to the mixture and was stirred for another 3 h before concentrating the reaction mixture under vacuum. The remaining residue was taken up in H20 (200 mL) and the unwanted solid was removed through filtration. The filtrate was concentrated and placed under vacuum to remove the remaining H20. The crude solid was taken up in CH2C12 (175 mL) and triethylamine (9.28 mL, 66.6 mmol) and Boc2O (4.86 g, 24.4 mmol) was added. After stirring for 12 h at room temperature, the reaction was quenched with a saturated solution of NaHCO3 (200 mL), extracted with CH2C12 (3 x 150 mL), dried over MgSO4, and concentrated under reduced pressure. The residue was purified using flash chromatography (10% to 45% ethyl acetate in hexanes) to provide the aryl pyridine ?IN? fragment (2.24 g, 43%): ?H-NMR (CDC13, 400 MHz) oe 7.78 (t, J = 7.6 Hz, 1H), 7.56 (d, J = 7.6 Hz, 1H), 7.49 (d, J= 8.0 Hz, 1H), 5.51 (s, 1H), 4.44 (d, J= 5.6 Hz, 2H), 1.43 (s, 9H); ?3C-NMR (CDC13, 100 MHz) 160.1, 155.9, 137.6, 133.0, 127.0, 125.1, 117.1, 79.9, 45.5, 28.3; JR (neat) 3347, 2979, 2934, 2239, 1699, 1518, 1453, 1250, 1170, 862; HRMS (ESI) mlz calcd for C12H15N3NaO3 [M+Na1 256.1062, found 256.1062.

The synthetic route of 135450-23-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; COLORADO STATE UNIVERSITY RESEARCH FOUNDATION; DANA-FARBER CANCER INSTITUTE, INC.; UNIVERSITY OF NOTRE DAME DU LAC; WILLIAMS, Robert, M.; BRADNER, James, E.; CLAUSEN, Dane; WIEST, Olaf, G.; NEWKIRK, Tenaya, L.; BOWERS, Albert, A.; GUERRA, Jennifer, Marie; (144 pag.)WO2016/144665; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem