Month: March 2022

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 139585-48-1, name is 2-Chloro-5-methoxypyridine. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C6H6ClNO

Carboxylic acid XIIIAcid XIII-I5 ‘-Methoxy-3,4,5,6-tetrahydro-2H- [ 1 ,2 ‘] bipyridinyl-4-carboxylic acida) 5′-Methoxy-3,4,5,6-tetrahydro-2H-[l,2’]bipyridinyl-4-carboxylic acid ethyl esterTo a stirred solution of piperidine-4-carboxylic acid ethyl ester (0.52 g, 3.34 mmol) and 2- chloro-5-methoxy-pyridine in 10 mL of toluene was added (13 mg, 0.057 mmol) of Pd(II) acetate, (17 mg, 0.027 mmol) of BINAP and tBuOK (0.44 g, 3.90 mmol). The mixture was heated at 1200C for two hours, concentrated under vacuo and the residue was directly purified on column chromatography (SiO2, EtOAc/Hept 1 :2) yielding 0.17 g (24 %) of the title compound as a light yellow oil. ES-MS m/e: 265.3 (M+H+).

With the rapid development of chemical substances, we look forward to future research findings about 139585-48-1.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; JABLONSKI, Philippe; KNUST, Henner; NETTEKOVEN, Matthias; PATINY-ADAM, Angelique; RATNI, Hasane; RIEMER, Claus; WO2011/23626; (2011); 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 1256811-02-5, name is 1-(5-Bromo-2-methoxypyridin-3-yl)ethanone. This compound has unique chemical properties. The synthetic route is as follows. Formula: C8H8BrNO2

Step 4-Synthesis of 2-bromo-1-(5-bromo-2-hydroxypyridin-3-yl)ethanone To a solution of 1-(5-bromo-2-methoxypyridin-3-yl)ethanone (2.0 g, 8.69 mmol) in HBr (20 mL, HOAc solution), Br2 (1.4 g, 8.76 mmol) was added dropwise at room temperature. The reaction mixture was stirred at room temperature for 5 hours. Then the reaction mixture was filtered to collect the HBr salt. The solid was suspended with Na2CO3 solution, extracted with EtOAc. The combined organic phases were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to provide 2-bromo-1-(5-bromo-2-hydroxypyridin-3-yl)ethanone (2.0 g, yield: 74%). 1H-NMR (DMSO, 400 MHz) delta 12.83 (br s, 1H), 8.11?8.13 (m, 2H), 4.85 (s, 2H). MS (M+H)+: 295.

With the rapid development of chemical substances, we look forward to future research findings about 1256811-02-5.

Reference:
Patent; Liverton, Nigel J.; McComas, Casey Cameron; Habermann, Joerg; Koch, Uwe; Narjes, Frank; Li, Peng; Peng, Xuanjia; Soll, Richard; Wu, Hao; Palani, Anandan; He, Shuwen; Dai, Xing; Liu, Hong; Lai, Zhong; London, Clare; Xiao, Dong; Zorn, Nicolas; Nargund, Ravi; US2014/213571; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 52311-20-3, 2-Amino-4-ethoxypyridine, 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, Safety of 2-Amino-4-ethoxypyridine, blongs to pyridine-derivatives compound. Safety of 2-Amino-4-ethoxypyridine

4-Ethoxy-pyridin-2-ylamine (15 g, 109 mmol) is dissolved in HOAc (100 mL) and cooled to 0 C. Bromine is added dropwise with vigorous stirring. The mixture is allowed to stir at RT for 30 minutes at which point a precipitate forms. The mixture is stirred for 30 min and the solids collected by filtration, washed with EtOAc in dried in a vacuum oven to give 5-bromo-4-ethoxy-pyridin-2-ylamine hydrobromide (23.3 g, 78.2 mmol).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,52311-20-3, 2-Amino-4-ethoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; Boehringer Ingelheim International GmbH; LIU, Pingrong; MILLER, Craig Andrew; YU, Maolin; ZHANG, Zhonghua; (93 pag.)US2018/72717; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 38222-83-2 , The common heterocyclic compound, 38222-83-2, name is 2,6-Di-Tert-butyl-4-methylpyridine, molecular formula is C14H23N, 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 mixture of 2, 6-di-/Patent; MASARYKOVA UNIVERZITA; PARUCH, Kamil; CARBAIN, Benoit; HAVEL, Stepan; DAMBORSKY, Jiri; BREZOVSKY, Jan; DANIEL, Lukas; SISAKOVA, Alexandra; NIKULENKOV, Fedor; KREJCI, Lumir; (190 pag.)WO2019/201865; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 52378-63-9, Adding some certain compound to certain chemical reactions, such as: 52378-63-9, name is (3-Aminopyridin-2-yl)methanol,molecular formula is C6H8N2O, 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 52378-63-9.

(i) A solution sodium nitrite (2.38 g.) in water (10 ml.) was added dropwise to a stirred mixture of 3-amino-2-hydroxymethylpyridine (4.8 g.) in aqueous hydrobromic acid (48%, 10 ml) and water (5 ml) at 0-5 C. This solution of the diazonium salt was added to a hot solution of cuprous bromide (2.5 g.) in 60% hydrobromic acid and following cessation of nitrogen evolution the mixture was heated on the steam bath for 0.5 hours, diluted with water and saturated with hydrogen sulphide. Filtration, concentration to low bulk and extraction with chloroform yielded 3-bromo-2-hydroxymethyl-pyridine (4.8 g.).

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. 52378-63-9, (3-Aminopyridin-2-yl)methanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Smith Kline & French Laboratories Limited; US4025527; (1977); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 179687-79-7, name is 2-((2-Chloro-4-nitrophenoxy)methyl)pyridine, molecular formula is C12H9ClN2O3, 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. HPLC of Formula: C12H9ClN2O3

General procedure: 10%Pt/C (0.40 g, 0.2 mmol) was added to a suspension of the nitro derivative (2a-2d)(1.7 mmol) in methanol (50.0 mL). The reaction mixture was stirred underhydrogen atmosphere at room temperature overnight. The mixture was thenfiltered through celite and the filtrate was evaporated under reduced pressureto afford the desired amines (3a-3d).

With the rapid development of chemical substances, we look forward to future research findings about 179687-79-7.

Reference:
Article; Elkamhawy, Ahmed; Farag, Ahmed Karam; Viswanath, Ambily Nath Indu; Bedair, Tarek M.; Leem, Dong Gyu; Lee, Kyung-Tae; Pae, Ae Nim; Roh, Eun Joo; Bioorganic and Medicinal Chemistry Letters; vol. 25; 22; (2015); p. 5147 – 5154;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 867279-13-8 , The common heterocyclic compound, 867279-13-8, name is 4-Bromo-2-chloro-5-methylpyridine, molecular formula is C6H5BrClN, 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 stirred solution of 4-bromo-2-chloro-5-methylpyridine (2 g, 9.69 mmol, 1 equiv.) in t- BuOH (15 mL) was added t-BuONa (2.0 g, 20.34 mmol, 2.1 equiv.) at room temperature. The final reaction mixture was irradiated with microwave radiation for 5 h at 120 degrees C. The reaction was monitored by LCMS. The mixture was allowed to cool down to room temperature. The reaction solution was acidified to pH 6 with HCl (aq.1M). The resulting mixture was extracted with CH2Cl2(3 x 50 mL). The combined organic layers were washed with brine (1×100 mL), dried over anhydrous Na2SO4. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by reverse phase flash with the following conditions (Column: C18 Column 330 g; Mobile Phase A: Water (10 mmol/L AcOH), Mobile Phase B: ACN; Flow rate: 80 mL/min; Gradient: 10% B to 30% B in 40 min; 254/220 nm) to afford 4- bromo-5-methylpyridin-2-ol(1.2g,65.89%) as an off-white solid.

The synthetic route of 867279-13-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GOLDFINCH BIO, INC.; YU, Maolin; DANIELS, Matthew, H.; HARMANGE, Jean-christophe, P.; TIBBITTS, Thomas, T.; LEDEBOER, Mark, W.; WALSH, Liron; MUNDEL, Peter, H.; MALOJCIC, Goran; (860 pag.)WO2019/55966; (2019); 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. 403-45-2, name is 6-Fluoronicotinic acid, the common compound, a new synthetic route is introduced below. Application In Synthesis of 6-Fluoronicotinic acid

A mixture of 6-fluoro-nicotinic acid (2.07g, 14.7mmol), K2CO3 (4.48g, 32.4mmol) and MeI (3.2Og, 22.5mmol) in DMF (6OmL) was stirred for 16h at rt. After dilution with H2O (5OmL), the reaction mixture was extracted with EtOAc (5OmL) and the extract washed successively with saturated NaHCO3 solution (2OmL), brine (2 x 2OmL) and dried (MgSO4). Filtration and evaporation of the solvent gave the product as an orange solid (1.79g, 78%). 1H (CDCl3) 8.53 (IH, s), 8.12 (IH, m), 6.77 (IH, dd), 3.67 (3H, s)

The synthetic route of 403-45-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JAMES BLACK FOUNDATION; WO2007/135350; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 183741-86-8, 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. 183741-86-8, name is 5-(Boc-amino)-2-methoxyisonicotinic Acid. A new synthetic method of this compound is introduced below.

[0615] Procedure: To a stirred solution of 5-((tert-butoxycarbonyl)amino)-2-methoxyisonicotinic acid (6.7 g, 24.974 mmol) in methanol / dichloromethane (6.7 mL / 67 mL) was added TMS-diazomethane (31.2 mL, 2.5 eq) at 0 C and the mixture was stirred at same temperature for 4 h. Reaction progress was monitored by TLC. Reaction mixture was concentrated, and residue was diluted with water, extracted using ethyl acetate (40 mL x 3), organic layer was dried over sodium sulphate, filtered and concentrated to give crude product. The crude product was purified by gradient column chromatography using ethyl acetate in n-hexane to afford methyl 5-((tert-butoxycarbonyl)amino)-2-methoxyisonicotinate as off-white solid (4.5 g, 63.82 %).1HNMR (400 MHz, CDCl3): delta 9.24 (bs, 1H), 9.18 (s, 1H), 7.23 (s, 1H), 3.93 (s, 3H), 3.92 (s, 3H), 1.52 (s, 9H). LC-MS (ES) m/z = 283.1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,183741-86-8, 5-(Boc-amino)-2-methoxyisonicotinic Acid, and friends who are interested can also refer to it.

Reference:
Patent; MAVUPHARMA, INC.; GALLATIN, William Michael; ODINGO, Joshua; DIETSCH, Gregory N.; FLORIO, Vincent; VENKATESHAPPA, Chandregowda; DURAISWAMY, Athisayamani Jeyaraj; (273 pag.)WO2019/46778; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 171197-80-1 ,Some common heterocyclic compound, 171197-80-1, molecular formula is C5H3FIN, 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 46; 5-Cyclopropyl-2-fluoro-pyridine; In a flask, combine 2-fluoro-5-iodo-pyridine (1.12 g, 5 mmol), cyclopropylboronic acid (645 mg, 7.5 mmol), palladium acetate (56 mg, 0.25 mmol), potassium phosphate (3.2 g, 15 mmol), and toluene-water (20: 1, 21 mL). Heat the mixture at 100 0C for 4 hours. Dilute the mixture with chloroform-isopropanol (3: 1, 100 mL). Wash the organic phase with saturated aqueous sodium chloride and water. Dry the mixture over sodium sulfate. Concentrate the solution in vacuo to a brown oil. Purify by column chromatography (20 % ethyl acetate in hexane) to afford the title compound (430 mg, 63 %) as a pale yellow oil. 1H nuMR (400 MHz-CDCl3) delta 7.99 (d, J= 3 Hz, IH), 7.39 (td, J= 3, 5 Hz, IH), 6.79 (dd, J= 3, 8 Hz, IH), 0.96-1.02 (m, 2H), 0.63-0.69 (m, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,171197-80-1, its application will become more common.

Reference:
Patent; ELI LILLY AND COMPANY; WO2008/76705; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem