Pyridine-derivatives

Synthetic Route of 934279-60-4 ,Some common heterocyclic compound, 934279-60-4, molecular formula is C7H3ClF3NO, 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.

2-chloro-5-trifluoromethylpyridine carbaldehyde (1.2g, 5.5mmol), obtained in step 1- 1 of Example 1 , was dissolved together with N-ethyl-N-(tetrahydro-2H-pyran-4-yl)-amine (1.3g, 16.5mmol) and K2C03 (3.03g, 22mmol), in toluene (15ml), and refluxed at 130C for 48 hrs with stirring. The reaction mixture cooled to room temperature, and added with water to terminate the reaction, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was purified by chromatography to afford the title compound ( .1g, 50%). 1H NMR (400MHz, CDCI3) 8.51 (s, 1 H), 7.88 (s, 1 H), 7.79 (d, J = 2.0Hz, 1 H), 7.77 (s, 2H), 5.72 (d, J = 8.0Hz, 1 H), 4.75 (d, J = 16.0Hz, 1 H), 4.34 (d, J = 16.0Hz, 1 H), 4.00 (m, 2H), 3.46 (m, 6H), 1.86 (m, 4H), 0.93 (t, 3H), 0.63 (d, 3H).

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. 934279-60-4, 2-Chloro-5-(trifluoromethyl)nicotinaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; DONG-A ST CO.,LTD; PARK, Jang Hyun; SONG, Seung Hyun; CHUNG, Han Kook; KIM, Heung Jae; LEE, Ji Hye; JANG, Byeong Jun; KIM, Eun Jung; JUNG, Hae Hum; RYU, Chae Lim; HWANG, Jae-Sung; LEE, Hyung Ki; KANG, Kyung Koo; KIM, Soon Hoe; WO2014/157994; (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. 197376-47-9, name is Ethyl 6-Chloropyridine-3-acetate. A new synthetic method of this compound is introduced below., name: Ethyl 6-Chloropyridine-3-acetate

To a solution of ethyl (6-chloropyridin-3-yl)acetate (1.0 g) in N,N-dimethylformamide (20 mL) was added sodium hydride (60% in mineral oil, 0.40 g) under ice-cooling, and the mixture was stirred for 40 min. To the reaction mixture was added 1-bromo-2-(2-bromoethoxy)ethane (2.3 g), and the mixture was stirred at 0 C. for 3 hr. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (0.82 g). (1596) MS(ESI+): [M+H]+ 270.1

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, 197376-47-9, Ethyl 6-Chloropyridine-3-acetate.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; Saitoh, Morihisa; Yogo, Takatoshi; Kamei, Taku; Tokunaga, Norihito; Ohba, Yusuke; Yukawa, Takafumi; (191 pag.)US2016/159773; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 62226-18-0, Adding some certain compound to certain chemical reactions, such as: 62226-18-0, name is 6-Chlorothieno[2,3-b]pyridine,molecular formula is C7H4ClNS, 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 62226-18-0.

EXAMPLE 70 6-Chloro-thieno[2,3-b]pyridine-2-sulfonyl chloride 6-Chloro-thieno[2,3-b]pyridine (0.73 g, 4.3 mmol) is to subjected to the three step sequence sequence described in EXAMPLE 8, Part A. Flash chromatography (15 % EtOAc/Hexane) of the crude product gives the title compound (0.75 g, 2.8 mmol): 1H NMR (CDCl3, 300 MHz) delta8.19 (d, 1H), 8.07 (s, 1H), 7.47 (d, 1H). EI MS M+=267, 269, 271.

According to the analysis of related databases, 62226-18-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Aventis Pharma Deutschland GmbH; US6281227; (2001); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 76015-11-7 ,Some common heterocyclic compound, 76015-11-7, molecular formula is C7H9NO2, 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.

a 2-Methyl-3-methoxy-4-chloropyridine N-oxide 11.2 g (80.5 mmol) of 3-methoxy-2-methyl-4(1H)-pyridone were heated under reflux for 10 hours in 100 ml of phosphorus oxychloride. Subsequently, the mixture was concentrated and 30 ml of toluene were added to each 2 ml volume; concentration then took place once again and the residue was taken up in 150 ml of water, with the pH of the mixture then being adjusted to 11 with K2 CO3; this mixture was then extracted with dichloromethane and the organic phase was washed with water, dried and freed from solvent. 8 g of the product were obtained, under standard conditions, from the pale brown oil (9 g) using m-chloroperbenzoic acid in dichloromethane, m.p. 88-89 C. (from petroleum ether).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,76015-11-7, its application will become more common.

Reference:
Patent; Hoechst Aktiengesellschaft; US5658933; (1997); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1186608-73-0, 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.1186608-73-0, name is 3-Methyl-1H-pyrazolo[3,4-b]pyridin-5-amine, molecular formula is C7H8N4, molecular weight is 148.17, as common compound, the synthetic route is as follows.

EXAMPLE 16: Tetra-butyl 3-(3-methyl-lH-pyrazolo r3.4-blpyridine-5- ylamino)piperidine- 1 -carboxylateTo a stirred solution of 3-Methyl-lH-pyrazole[3,4-¾]pyridn-5-amine (500mg, 3.3mmol) in EtOH (50ml), tert-butyl 3 -oxopiperidine-1 -carboxylate (74mg, l . lmmol) was added and reaction mass was cooled to 0C. Acetic acid (0.018ml, 0.33mmol) was added after which reaction mixture was stirred for 20 minutes. Sodium cyanoborohydride (42mg, 0.66mmol) was added and stirred for 12h at RT. TLC showed absence of SM. The reaction mixture was quenched with brine solution and extracted with ethyl acetate. The extract was washed with water and concentrated. Organic layer was dried over anhydrous sodium sulphate, dried and concentrated. Product was purified by flash column chromatography over 230-400 mesh silica gel using 2-5% MeOH/ DCM as eluent to afford the desired product 20, 500mg (Yield: 45%) as white solid. The product was confirmed by 1HNMR and MS spectrum analysis. 1H NMR (400 MHz, CDC13) delta: 8.13 (s, 1H), 7.19 (s, 1H), 3.95 (m, 1H), 3.25 (m, 1H), 3.43 (m, 1H), 3-3.25 (m, 2H), 2.52 (s, 3H), 2.15 (m. 1H), 1.78 (m, 1H), 1.6 (m, 2H), 1.49 (s, 9H); Ms- 331 (M-56), LCMS- 97%.

Statistics shows that 1186608-73-0 is playing an increasingly important role. we look forward to future research findings about 3-Methyl-1H-pyrazolo[3,4-b]pyridin-5-amine.

Reference:
Patent; ARRIEN PHARMAEUTICALS LLC; VANKAYALAPATI, Hariprasad; APPALANENI, Rajendra, P.; REDDY, Y., Venkata Krishna; WO2012/135631; (2012); 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 197376-47-9, name is Ethyl 6-Chloropyridine-3-acetate. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of Ethyl 6-Chloropyridine-3-acetate

Step 2 To a solution of ethyl 2-(6-chloropyridin-3-yl)acetate (1.1 g, 5.51 mmol) in dimethylformamide was added slowly sodium hydride (242 mg, 6.06 mmol) at 0 C., followed by iodomethane (821 mg, 5.79 mmol). The mixture was stirred at same degree for 1 hour, and then quenched with water. The resulting mixture was diluted with ethyl acetate and washed with water. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure to afford crude which was purified by column chromatography to afford ethyl 2-(6-chloropyridin-3-yl)propanoate (790 mg, 67%).

With the rapid development of chemical substances, we look forward to future research findings about 197376-47-9.

Reference:
Patent; Gruenenthal GmbH; FRANK, Robert; BAHRENBERG, Gregor; CHRISTOPH, Thomas; LESCH, Bernhard; LEE, Jeewoo; US2013/29962; (2013); 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. 55849-30-4, name is 5-Bromo-2-ethoxypyridine, the common compound, a new synthetic route is introduced below. Safety of 5-Bromo-2-ethoxypyridine

General procedure: PdCl2(dppf), PdCl2(tbpf) and (A.caPhos)PdCl2. A mixture of the halogenated heterocycle (0.66 mmol) in anhydrous THF (13.2 mL) was degassed by bubbling argon for few minutes. Then, PdCl2(dppf) (27.0 mg, 0.033 mmol, 5.0 mol%), TMEDA (0.130 g, 1.12 mmol, 1.7 equiv) and finally NaBH4 (42.4 mg, 1.12 mmol, 1.7 equiv) were introduced in sequence. The mixture was stirred at room temperature under argon for the proper time and then worked up as described above.

The synthetic route of 55849-30-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chelucci, Giorgio; Figus, Susanna; Journal of Molecular Catalysis A: Chemical; vol. 393; (2014); p. 191 – 209;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1033810-70-6 , The common heterocyclic compound, 1033810-70-6, name is [1,2,4]Triazolo[1,5-a]pyridin-7-ol, molecular formula is C6H5N3O, 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.

Step F: Preparation of tert-butyl 4-([1,2,4]triazolo[1,5-a]pyridin-7-yloxy)-3-chloro-2-fluorobenzoate: A vial charged with tert-butyl 3-chloro-2,4-difluorobenzoate (0.210 g, 0.845 mmol), [1,2,4]triazolo[1,5-a]pyridin-7-ol (0.114 g, 0.845 mmol), cesium carbonate (0.413 g, 1.27 mmol), and DMF (1.7 ml). The reaction was heated to 80 C for 12 hours, then poured into ice water. The resulting solids were collected by filtration and purified by flash chromatography, eluting with gradient of 10% EtOAc/ Hexanes to 50% EtOAc/Hexanes to provide the desired product.

The synthetic route of 1033810-70-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Array Biopharma, Inc.; EP2090575; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 83766-88-5, 2-(tert-Butoxy)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, Quality Control of 2-(tert-Butoxy)pyridine, blongs to pyridine-derivatives compound. Quality Control of 2-(tert-Butoxy)pyridine

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.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,83766-88-5, 2-(tert-Butoxy)pyridine, and friends who are interested can also refer to it.

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

Related Products of 846036-96-2, 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.846036-96-2, name is (4-Amino-6-chloropyridin-3-yl)methanol, molecular formula is C6H7ClN2O, molecular weight is 158.59, as common compound, the synthetic route is as follows.

Manganese dioxide (230 g, 2648 mmol) was added to a solution of (4-amino-6- chloropyridin-3-yl)methanol (50 g, 265 mmol) in dichloromethane (3000 mL) at 0 C under nitrogen. The resulting reaction mixture was allowed to warm to room temperature and stirred for sixteen hours. On completion, the reaction mixture was filtered through a Celite pad and the residue was washed with dichloromethane and the filtrate was evaporated under reduced pressure. The solid was washed with pentane to afford 4-amino-6-chloronicotinaldehyde (41 g, 237 mmol, 89 % yield) as an off white solid. 1H NMR (400 MHz, CD3SOCD3) delta 6.73 (s, 1 H), 7.69-7.91 (m, 2 H), 8.43 (s, 1 H), 9.88 (s, 1 H); LC-MS (LC-ES) M+H = 157.

Statistics shows that 846036-96-2 is playing an increasingly important role. we look forward to future research findings about (4-Amino-6-chloropyridin-3-yl)methanol.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; DEATON, Dave Norman; SHEARER, Barry George; YOUNGMAN, Mark Andrew; (214 pag.)WO2018/229629; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem