Day: April 20, 2022

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.22280-60-0, name is 6-Chloro-2-methyl-3-nitropyridine, molecular formula is C6H5ClN2O2, molecular weight is 172.57, as common compound, the synthetic route is as follows.name: 6-Chloro-2-methyl-3-nitropyridine

Preparation 6 2-Methoxy-5-Nitro-6-Methylpyridine Sodium metal (8.68 g, 378 mmol) was added to methanol (350 mL) pre-cooled to 0 C. After the sodium completely dissolved, 2-chloro-5-nitro-6-methylpyridine (40.78 g, 236 mmol) was slowly added as a solid. The reaction mixture was heated at reflux temperature overnight, then poured into ice-water. The product was filtered and dried in vacuo overnight to give 29.39 grams of the title compound. (73%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,22280-60-0, 6-Chloro-2-methyl-3-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; Eli Lilly and Company; US6358972; (2002); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 82523-07-7, Adding some certain compound to certain chemical reactions, such as: 82523-07-7, name is Methyl 3H-imidazo[4,5-c]pyridine-6-carboxylate,molecular formula is C8H7N3O2, 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 82523-07-7.

Cooling in the ice bath,5g (28.22mmol) of 3H-imidazo[4,5-c]pyridine-6-carboxylate40mL NaOH aqueous solution (2M) dissolved,After 4 h of reaction, the reaction mixture was adjusted to pH 7 with dilute hydrochloric acid (2M).Allow to stand and allow the solid to be analyzed. Filter, filter and wash with distilled water, dry,Yield 1.757 g (38%) of the title compound.It is a pale yellow solid.

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. 82523-07-7, Methyl 3H-imidazo[4,5-c]pyridine-6-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Capital University of Medical Sciences; Zhao Ming; Peng Shiqi; Wang Yuji; Wu Jianhui; Gui Lin; Wang Yongjian; (13 pag.)CN108976225; (2018); A;,
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. 33252-28-7, name is 6-Chloronicotinonitrile, the common compound, a new synthetic route is introduced below. Formula: C6H3ClN2

A 185 ml stirred autoclave was charged under argon with PdC12(dppp) (213 mg, 0.36 1 mmol), 6- chloro-nicotinonitrile (10 g, 72.2 mmol), dioxane (50 ml), deionized water (50 ml) and sodium, bicarbonate (15.2 g, 0.18 mol, 2.5 molar equivalents). The reaction vessel was closed, purged three times with carbon monoxide (15 bar) and finally charged with carbon monoxide to 60 bar. The mixture was stirred vigorously at 60C under constant pressure for 22 h; after this time no more carbon monoxide absorption was observed. The reaction mixture was transferred to a5 round-bottomed flask with aid of water and, after having removed the organic volatilecomponents on a rotary evaporator, the reaction mixture was worked-up as reported in Example1. Crystallization afforded 5-cyano-pyridine-2-carboxylic acid (9.55 g) as a white solid with 99.6a% purity by HPLC.Example 5a-h5-Cyano-pyridine-2-carboxylic acid A series of reaction conditions was tested using the same procedure described in Example 4. The results are included in the following table.Ex.PbarTCBase ImolarequivalentsSolvent Ivol/volratio2-Cl,5-CN-Py[a%]3-CN-Py-2-C0211[a % I3-CN-Py[a%]Isol.Yield(%)5a6060Na2CO31.25Water 1Dioxane 10.293.51.6895b6060NaOAc2.5Water 1Acetone 13.683.57.9n.d.5c4060Et3N2.5Water 1 t-BuOH 10.795.91.0895d1560Et3N2.5Water 1t-BuOH 4<0.195.41.992Se70100Et3N2.2Water 1THF40.453.825n.d.Sf3580Et3N2.5Water 1 CH3CN 4<0.193.54.9n.d.Sg3580Et3N2.5Water 1CH3CN 4MeOH 1<0.191.51.5n.d.5h4050Et3N2.5Water 1t-BuOH 110.586.60.5n.d.Example no. Sc: reaction time S h; example no. Sd and Sh: reaction time 16 h; example no. Sf:reaction time 12 h.Examples no. Se and Sf: S g of 2-Cl,S-CN-Py, S/C 330.Example no. Sg: crude mixture contains 3.7 a% of the methyl ester 3-CN-Py-2-CO2Me. a% S values are obtained by HPLC analysis. The synthetic route of 33252-28-7 has been constantly updated, and we look forward to future research findings. Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; FETTES, Alec; MARTY, Hans-Peter; SCALONE, Michelangelo; WO2014/173917; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 59942-87-9, Pyrazolo[1,5-a]pyridin-2(1H)-one, 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 Pyrazolo[1,5-a]pyridin-2(1H)-one, blongs to pyridine-derivatives compound. Safety of Pyrazolo[1,5-a]pyridin-2(1H)-one

To a solution of 4a (3.10 g, 23.1 mmol) in THF (17 mL) and DMF (17mL) was added NaH (1.0 g, 25.4 mmol, 60% dispersion in oil) and Tf2NPh (9.90 g, 27.7 mmol) at 0 C. The mixture was stirred for 1 h, then it was added to ice-water and extracted with EtOAc. The organiclayer was washed with brine and dried (Na2SO4). The mixture was concentrated in vacuo. The crude material was purified by flash column chromatography (silica gel, hexane-EtOAc, 10:1) to give 3a as acolorless solid; yield: 6.10 g, 99%); mp 37-38 C.

The synthetic route of 59942-87-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Umei, Kentaro; Nishigaya, Yosuke; Kamiya, Megumi; Kohno, Yasushi; Seto, Shigeki; Synthesis; vol. 47; 20; (2015); p. 3221 – 3230;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 182275-70-3, Adding some certain compound to certain chemical reactions, such as: 182275-70-3, name is 2-Iodo-6-methoxypyridine,molecular formula is C6H6INO, 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 182275-70-3.

(-)-P7C3-S243: (S)-N-(3-(3,6-dibromo-9H-carbazol-9-yl)-2-fluoropropyl)-3-methoxyaniline: (S)-9-(3- amino-2-fluoropropyl)-3,6-dibromo-9H-carbazole (72.2 mg, 0.18 mmol), 2-iodo-6-methoxypyridine 45.4 mg, 0.19 mmcl), copper iodide (2.9 mg, 0.015 mmcl) and cesium carbonate (119.4 mg, 0.36 mmcl) were added to an oven dried vial, which was nitrogen purged for 10 minutes. DMSO (0.36and 2,2,6,6-tetramethyl-3,5-heptanedione (4 il, 0.019 mmcl) were then added. The reaction was heated at 40 C for three hours. The cooled mixture was diluted with EtOAc and washed thrice witha solution of 9:1 saturated NH4CI: NH4OH and then thrice with water and then brine. The organic layer was dried over Na2SO4, filtered and concentrated. The well dried solid was dissolved in methylene chloride and passed through a short silica plug, which removed the small amount of unreacted amine. The filtrate was condensed to give white solid, which was purified by automated flash chromatography system in 50-80 % methylene chloride/hexanes. Isolated yield = 61%, ee =96%. Recrystallization to enhance ee was carried out by heating a solution of 15.8 mg of purified product in 1.0 ml of isopropanol. Overall Yield = 59 %, ee = 98.5 %1H NMR (CDCI3, 400 MHz) :5 8.16 (d, J = 1.9 Hz, 2H), 7.56 (d, J = 1.9 Hz, 2H), 7.35 – (t, J = 7.8 Hz, 1H),7.30 (d, J = 8.7 Hz, 1H), 6.04 (dd, J = 32.7, 8.0 Hz, 2H), 5.29 -5.02 (dm, 1H), 4.65 -4.46 (m, 3H), 3.87- 3.74 (m, 1H), 3.70 (s,3H), 3.66 – 3.49 (m, 1H). ESI m/z: 506.7 ([Mi-1], C22H19Br2FN2O requires504.98

According to the analysis of related databases, 182275-70-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOARD OF REGENTS OF THE UNIVERSITY OF TEXAS SYSTEM; UNIVERSITY OF IOWA RESEARCH FOUNDATION; MCKNIGHT, Steven L.; READY, Joseph M.; PIEPER, Andrew A.; WO2015/70234; (2015); A3;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 65515-39-1 , The common heterocyclic compound, 65515-39-1, name is 2-Methoxy-4,6-dimethylnicotinonitrile, molecular formula is C9H10N2O, 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-methoxy-6-methyl-4-(pent-4-en- -yl)nicotinonitrile To a solution of 2-methoxy-4,6-dimethylnicotinonitrile (2.5 g, 15.41 mmol) in THF (80 mL) was added LHMDS (1 M in THF, 16.18 mL, 16.18 mmol) at 0 C dropwise via dropping funnel over 10 min, and the reaction mixture turned an orange color. The mixture was stirred at 0 C for 50 min, then 4-bromobut-l-ene (1.878 mL, 18.50 mmol) was added dropwise via syringe and the mixture was stirred from 0 C to 10 C for 2.5 h. The reaction mixture was quenched with saturated aqueous ammonium chloride solution (40 mL) and the layers were separated and the aqueous layer was extracted with EtOAc (3x). The combined organics were concentrated and the residue adsorbed onto silica and purified by flash chromatography (CombiFlash, 0-5% EtOAc in hexane, 80 g column) to afford 2-methoxy-6-methyl-4-(pent-4-en-l-yl)nicotinonitrile (1.3 g, 6.01 mmol, 39.0% yield) as a colorless oil. LC-MS(ES) m/z = 217.0 [M+H]+.

The synthetic route of 65515-39-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; KNIGHT, Steven David; LAFRANCE, Louis Vincent III; MCNULTY, Kenneth C.; ROMERIL, Stuart Paul; SEEFELD, Mark Andrew; WO2014/195919; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 2897-43-0, 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. 2897-43-0, name is 2,6-Dichloro-3-nitropyridin-4-amine, molecular formula is C5H3Cl2N3O2, 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.

To a solution of 2,6-dichloro-3-nitropyridin-4-amine in ethanol (150 mL) was added iron powder (14.3 g, 0.255 mol), water (46 mL), and then concentrated HCl (28 mL). The reaction mixture was then stirred at 95 C. for 16 hours, cooled to room temperature, and neutralized. The precipitates were collected by filtration and dried in vacuo. The crude product was then treated with water (200 mL) and extracted with EtOAc (3*200 mL). The combined extracts were dried over anhydrous Na2SO4, filtered, and concentrated to afford 7.85 g of the title compound (86.5% yield).

According to the analysis of related databases, 2897-43-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; HUTCHISON MEDIPHARMA LIMITED; Su, Wei-Guo; Deng, Wei; Ji, Jianguo; US2014/121200; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1190319-62-0, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 1190319-62-0 as follows.

Step 4: A solution of 6?-bromospiro[cyclopropane-l ,3?-pyrrolo[3,2-b]pyridin]-2?(1 H)-one (5.7 g, 24.6 mmol) in dry DMF (10 mL) was added dropwise to a stirred suspension NaH (60% dispersion in oil, 5.91 g, 148 mmol) in dry DMF (50 mL) under Ar at 0C. After complete addition, the mixture was stirred for 15 mm before dropwise addition of a solution of I ,2-dibromoethane (6.36 mL, 73.8 mmol) in dry DMF (10 mL).The brown reaction mixture was stirred at rt for 18 h. The mixture was reduced in volume and diluted with EtOAc (100 mL) and water (100 mL). The layers were separated and the aqueous layer was extracted with EtOAc (2x 100 mL). The combined organic layer was washed with brine, dried over Na2SC4 and evaporated. Purification by column chromatography (silica, 33% EtCAc in heptane), followed by titruation from CH2CI2 afforded 6?-bromospiro[cyclopropane-l ,3?-pyrrolo[3,2-b]pyridin]-2?(1 ?H)-one (3.62 g,14.4 mmol, 58%) as a yellow solid. LCMS: calculated for [M+H]: 241, found: 241, isotope pattern present.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1190319-62-0, its application will become more common.

Reference:
Patent; GRUeNENTHAL GMBH; NARDI, Antonio; JAKOB, Florian; KONETZKI, Ingo; CRAAN, Tobias; HESSLINGER, Christian; DOODEMAN, Robin; (0 pag.)WO2016/8593; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 124236-37-9, 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. 124236-37-9, name is Methyl 5-(trifluoromethyl)picolinate. A new synthetic method of this compound is introduced below.

[00173] Urea-H202 (161 mg, 1.72 mmol) was added into a solution of 56 (100 mg, 0.49 mmol) in DCE (4 mL). Trifluoroacetic anhydride (281 mg, 1.35 mmol) was added at -10 C for 2 h. The reaction mixture was stirred at 0 C for 2 h and then at rt overnight. The mixture was poured into ice-water (10 mL) and adjusted to pH 6-7 with 30% sodium hydroxide solution. The mixture was extracted with ethyl acetate (5 mL X 3). The combined organic layers were dried over anhydrous Na2504, filtered and concentrated under reduced pressure to afford 57 (50 mg, 46%) as a yellow solid, which was used for the next step directly without further purification. LC-MS tR = 0.372 mm in 5-95AB_1.5 mm chromatography (Welch MK RP-18e 25-2mm), MS (ESI) m/z 221.8 [M + H].

At the same time, in my other blogs, there are other synthetic methods of this type of compound,124236-37-9, Methyl 5-(trifluoromethyl)picolinate, and friends who are interested can also refer to it.

Reference:
Patent; VITAE PHARMACEUTICALS, INC.; CLAREMON, David, A.; DILLARD, Lawrence, Wayne; DONG, Chengguo; FAN, Yi; JIA, Lanqi; LOTESTA, Stephen, D.; MARCUS, Andrew; SINGH, Suresh, B.; TICE, Colin, M.; YUAN, Jing; ZHAO, Wei; ZHENG, Yajun; ZHUANG, Linghang; WO2014/179564; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 76015-11-7, 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 76015-11-7, name is 3-Methoxy-2-methylpyridin-4(1H)-one. This compound has unique chemical properties. The synthetic route is as follows.

In a four-necked flask equipped with a mechanical stirrer, a reflux condenser, and a thermometer,230 grams of phosphorus oxychloride, 27.8 grams of 3-methoxy-2-methyl-4-pyrone, stirring slowly heated to 60-70 C, heat 10h,Cooling to 0-10 C, adding 60 g DMF, stirring 2h, layered,The lower organic layer was collected to give Vilsmeier reagent.The upper layer was poured into 50 g of ice-water mixture and the hydrolysis temperature was controlled at -5-5 C.Stirring 1h hydrolysis is complete, with 30% liquid alkali 20-30 adjust the pH to 12,Extracted with methylene chloride,Distillation gave the desired product4-Chloro-3-methoxy-2-methyl-4-pyridin 26.5 g,Using 3-methoxy-2-methyl-4-pyrone meter, mass yield of 95.3%.

According to the analysis of related databases, 76015-11-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; jiangsu yuxiang chemical co. ltd; Zhejiang University of Science and Technology; LI, GUONENG; Zhang, ZHIGUO; Cheng, Yun Tao; Zhong, Xu Hui; Li, Qing Long; Cheng, hongweid; (7 pag.)CN103483248; (2016); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem