Tag: M.W:100-200

Reference of 16063-69-7, Adding some certain compound to certain chemical reactions, such as: 16063-69-7, name is 2,4,6-Trichloropyridine,molecular formula is C5H2Cl3N, 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 16063-69-7.

2,4,6-Trichloropyridine (5 g, 27.4 mmol) in anhydrous THF (100 ml) was cooled to -78 C. A solution of n-butyllithium (22.27 ml, 28.8 mmol) (1.6M in hexane) was added slowly at -78 C. The solution was stirred at -78 C. for 30 mins, then treated with a solution of ethyl formate (10.15 g, 137 mmol) maintaining an internal temperature below -74 C. The resulting solution was stirred at -78 C. until all starting material was consumed (monitored by TLC, 9:1 heptane/EtOAC), then it was quenched at -78 C. with a solution of saturated ammonium chloride and 50 ml 0.5N aq. HCl under vigorous stirring. It was then allowed to warm to r.t. The quenched mixture was extracted with EtOAc, the organic phase was washed with brine, dried over MgSO4, and concentrated. The crude residue (light yellow solid) was purified by flash chromatography on silica gel with 0-20% EtOAc/heptane to provide 5.1 g (88% yield) of the desired 2,4,6-trichloronicotinaldehyde as a white solid. 1H NMR (400 MHz, chloroform-d3) delta ppm=10.42 (s, 1H), 7.45 (s, 1H).

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. 16063-69-7, 2,4,6-Trichloropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; BARBE, Guillaume; BEBERNITZ, Gregory Raymond; GENG, Sicong; GULGEZE EFTHYMIOU, Hatice Belgin; LIAO, Lv; MA, Fupeng; MO, Ruowei; PARKER, David Thomas; PENG, Yunshan; PEUKERT, Stefan; YAMADA, Ken; YASOSHIMA, Kayo; (78 pag.)US2018/111932; (2018); 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 875781-17-2, name is 5-Bromo-1H-pyrazolo[3,4-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C6H4BrN3

Step 1 5-bromo-1-methyl-1H-pyrazolo[3,4-b]pyridine (Compound 4-2) Sodium hydride (720 mg, 30 mmol) was added into a 100 ml reaction flask, and anhydrous THF (40 mL) was added to the reaction flask. After stirring at 0 C. for 5 min, the reaction substrate 5-bromo-1H-pyrazolo[3,4-b]pyridine (4.0 g, 20 mmol, commercially available) was dissolved in THF (20 ml), and the resulting solution was slowly added dropwise to the reaction flask through the constant pressure funnel, and stirred for 30 min. Afterwards, iodomethane (1.6 ml, 26 mmol) was added dropwise to the reaction system. After completion of the addition, the reaction solution was slowly warmed to room temperature and stirred overnight. The reaction progress was monitored by TLC. After completion of the reaction, 10 ml of ice water was added to the reaction system to quench the reaction, THF was removed by concentration under reduced pressure, and the residue was extracted with dichloromethane (60 ml) and water (20 ml*3). The organic layer was dried over anhydrous Na2SO4, and concentrated under reduced pressure to give 4.1 g brown solid, which was separated and purified by Combi-flash chromatography [PE:EA=10:90-40:60] to give the title compound 4-2 (3.1 g, 73%). MS m/z (ESI): 211.9 [M+H]+.

With the rapid development of chemical substances, we look forward to future research findings about 875781-17-2.

Reference:
Patent; SHANGHAI HAIYAN PHARMACEUTICAL TECHNOLOGY CO. LTD.; YANGTZE RIVER PHARMACEUTICAL GROUP CO., LTD.; LAN, Jiong; JIN, Yunzhou; ZHOU, Fusheng; XIE, Jing; SHEN, Sida; HU, Yi; LIU, Wei; LV, Qiang; (96 pag.)US2017/8889; (2017); 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. 871836-51-0, name is 4-Chloro-1H-pyrazolo[4,3-c]pyridine. A new synthetic method of this compound is introduced below., category: pyridine-derivatives

Intermediate 153-Bromo-4-chloro-1H-pyrazolo[4,3-c]pyridineN-bromosuccinimide (1.87 g, 10.5 mmol) was added to a solution of Intermediate 11 (1.61 g, 10.5 mmol) in acetonitrile (50 ml), and the mixture was heated to reflux for 3 h. The solvents were evaporated and DCM (60 ml) was added to the crude solid and the mixture stirred at r.t. for 30 min. The beige solid was filtered off, washed with DCM, then dried under vacuum (1.98 g, 81percent). 1H NMR (400 MHz, DMSO-c/6) delta ppm 7.69 (d, J=6.0 Hz, 1 H), 8.22 (d, J=6.0 Hz, 1 H); m/z (ES+APCI)+: 232 / 234 / 236 [M + H]+.

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, 871836-51-0, 4-Chloro-1H-pyrazolo[4,3-c]pyridine.

Reference:
Patent; MEDICAL RESEARCH COUNCIL TECHNOLOGY; MCIVER, Edward, Giles; SMILJANIC, Ela; HARDING, Denise, Jamilla; HOUGH, Joanne; WO2010/106333; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 58481-11-1, 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. 58481-11-1, name is Methyl 2-chloroisonicotinate, molecular formula is C7H6ClNO2, 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.

In a dried flask was zinc powder (3.05 g, 46.69 mmol) suspended in anhydrous tetrahydrofuran (25 mL) under nitrogen. The resulting suspension was warmed to 60° C., then 1,2-dibromoethane (0.168 mL, 1.95 mmol) was added and stirred at that temperature for 15 min. It was cooled to room temperature, then chlorotrimethylsilane (0.2 mL, 1.58 mmol) was added and stirred at room temperature for 1 h 15 min. Then, 4-(bromomethyl)-2-fluoro-1-(trifluoromethyl)benzene (10 g, 38.91 mmol) in tetrahydrofuran (5 mL) was added in 6 equal portions every 10 minutes under ice-cooling. After complete addition the ice-bath was removed and the reaction mixture stirred at room temperature for 18 h. Then was stirring switched off to let the solids settle. The supernatant was used in next transformation. To a solution of methyl 2-chloroisonicotinate (5.15 g, 30 mmol) and Pd(PPh3)4 (0.693 g, 0.60 mmol) in tetrahydrofuran (40 mL) under nitrogen in a dried flask was added freshly prepared (3-fluoro-4-(trifluoromethyl)benzyl)zinc(II) bromide (12.55 g, 38.91 mmol) in tetrahydrofuran (50 mL). The resulting bright yellow mixture was heated to 60° C. for 2 h 20 min, then cooled to room temperature. The reaction was quenched by the addition of 10percent NH4Cl. It was diluted with ethyl acetate. After phase separation, the organic layer was washed with brine, dried over MgSO4 and evaporated. The residue was suspended in 150 mL MTBE and sonicated, then the yellow insolubles were filtered off and washed with MTBE. The volume of the filtrate was increased to ca. 200 mL, then hydrogen chloride (7.50 mL, 30.00 mmol) (4M in dioxane) was added dropwise. A colorless precipitate formed. The resulting suspension was stirred for ca. 1 h, then sonicated for 2 min. The formed solid was collected and washed with MTBE and dried. The solid was dissolved in DCM and washed with 10percent K2CO3. After phase separation, the aqueous layer was extracted with DCM. The combined organic layers were dried over MgSO4 and evaporated. Methyl 2-(3-fluoro-4-(trifluoromethyl)benzyl)isonicotinate (8.26 g, 88percent) was isolated as a pale orange oil. 1H NMR (400 MHz, cdcl3) delta 3.94 (s, 3H), 4.24 (s, 2H), 7.06-7.18 (m, 2H), 7.52 (t, 1H), 7.69-7.75 (m, 2H), 8.68-8.75 (m, 1H). MS m/z 314 (M+H)+

According to the analysis of related databases, 58481-11-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AstraZeneca AB; US2010/261755; (2010); A1;,
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. 68470-59-7, name is 2-(Bromomethyl)-6-methylpyridine, molecular formula is C7H8BrN, 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. Safety of 2-(Bromomethyl)-6-methylpyridine

Step A: Preparation of 4-methyl-3-[2-methyl-4-(6-methyl-pyridin-2-ylmethoxy)-6-oxo-6H-pyrimidin-1-yl]-benzoic acid methyl ester To a solution of Intermediate 2 (460 mg, 1.68 mmol) in N,N-dimethylformamide (2 mL) was added 2-(bromomethyl)-6-methylpyridine (312 mg, 1.68 mmol), potassium carbonate (350 mg, 2.53 mmol) and 18-crown-6 (40 mg). The slurry was stirred at ambient temperature for one hour. The reaction was partitioned between ethyl acetate and water. The organic layer was washed with water and brine and dried over magnesium sulfate. The slurry was filtered and concentrated in vacuo. The crude material was purified using normal phase chromatography (ethyl acetate/heptane) to provide the alkylated product as a white semi-solid (100 mg, 16% yield). MS (M+H): 380

With the rapid development of chemical substances, we look forward to future research findings about 68470-59-7.

Reference:
Patent; CONFLUENCE LIFE SCIENCES, INC.; SELNESS, Shaun R.; Devadas, Balekudru; Hockerman, Susan L.; Monahan, Joseph B.; US2013/143906; (2013); 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. 15128-82-2, name is 2-Nitropyridin-3-ol. A new synthetic method of this compound is introduced below., HPLC of Formula: C5H4N2O3

To an ice-cold solution of 2-nitropyridin-3-ol (10.0 g, 71 mmol) and triethylamine (14.9 ml, 107 mmol) in methylene chloride (150 ml) was added, dropwise, triflic anhydride (14.5 ml, 86 mmol) and the mixture was stirred for 2h. Water was added and the mixture extracted with methylene chloride. The organic phase was dried with sodium sulfate and the solvent was evaporated in vacuo. The residue was purified by column chromatography on silica gel using n-heptane/ethyl acetate (v/v 2:8 to 3:7) as eluent. The title compound was obtained as a light brown liquid (18.4 g, 95%).MS ISP (m/e): 273.1 [(M+H)+].1H NMR (CDCI3, 400 MHz): delta (ppm) = 8.65 (dd, 1H), 8.00 (dd, 1H), 7.80 (dd, 1H).

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, 15128-82-2, 2-Nitropyridin-3-ol.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BAUMANN, Karlheinz; GOETSCHI, Erwin; GREEN, Luke; JOLIDON, Synese; KNUST, Henner; LIMBERG, Anja; LUEBBERS, Thomas; THOMAS, Andrew; WO2011/92272; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1480-65-5 , The common heterocyclic compound, 1480-65-5, name is 5-Chloro-2-fluoropyridine, molecular formula is C5H3ClFN, 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 suspension of 5-chloro-2-fluoropyridine 4d (5.00g, 38.0mmol) and guanidine carbonate (20.5g, 114mmol) in NMP (50mL) was added K2CO3 (26.3g, 190mmol), and the mixture was heated to 130°C and stirred for 8h. To the mixture at room temperature were added EtOAc (100mL) and H2O (200mL), and the layers were separated. The aqueous layer was extracted with EtOAc (3×100mL), and the combined organic layer was washed with 10percent aqueous NaCl (3×50mL) and concentrated in vacuo. To the resulting residue was added EtOAc (500mL), and the solution was filtered through a pad of NH silica gel. The filtrate was evaporated, and the residue was suspended in EtOAc/ hexane (1:3, 40mL). The mixture was stirred at 40°C for 1h. The mixture was cooled to room temperature and stirred for 1h, and then filtered. The obtained solids were dissolved into H2O (15mL) at 50°C, and the solution was gradually cooled to room temperature. The slurry was stirred at room temperature for 1h, and then filtered to give 5d (3.03g, 47percent) as a white solid. Mp 162?163°C; 1H NMR (500MHz, DMSO-d6) delta 6.60 (dd, J=8.8, 0.6Hz, 1H), 6.75 (br s, 4H), 7.48 (dd, J=8.8, 2.8Hz, 1H), 8.04 (d, J=2.5Hz, 1H); 13C NMR (125MHz, DMSO-d6) delta 119.3, 120.0, 136.5, 143.7, 157.6, 162.1; IR (ATR) 3468, 3414, 2362, 1627, 1573, 1543, 1518, 1463, 1370, 1314, 1278, 1229, 1133, 1110, 1004, 914, 857, 834, 756, 730, 614, 572, 520, 459, 436, 405cm?1; HRMS-ESI (m/z): [M+H]+ calcd for C6H8ClN4 171.0437; found, 171.0432.

The synthetic route of 1480-65-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ishimoto, Kazuhisa; Nagata, Toshiaki; Murabayashi, Mika; Ikemoto, Tomomi; Tetrahedron; vol. 71; 3; (2015); p. 407 – 418;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 18820-82-1, 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. 18820-82-1, name is Pyridine hydrobromide. A new synthetic method of this compound is introduced below.

A 5 mL water solution of NiCl2*6H2O (0.5950 g, 2.50 mM) was added into 10 mL methanol solution of Na2tdas (0.9710 g, 5.00 mM), and the solution was stirred for one hour. The solution above was then added into 10 mL water solution of N-hydrogenpyridinium bromide (0.8000 g, 5.00 mM), and the mixture was stirred for ten minutes, during which a brownish sediment appeared. Brownish microcrystals were obtained after recrystallization of the brownish sediment from diethyl ether.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,18820-82-1, Pyridine hydrobromide, and friends who are interested can also refer to it.

Reference:
Article; Wang, Chi-Feng; Qiao, Fang; Chi, Yan-Hui; Shi, Jing-Min; Cottrill, Ethan; Pan, Ning; Zhu-Ge, Wei-Wei; Fu, Yong-Xin; Xu, Jun; Qian, Xiao-Ping; Journal of Coordination Chemistry; vol. 68; 21; (2015); p. 3884 – 3893;,
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. 78790-79-1, name is 3-Amino-4-cyanopyridine, the common compound, a new synthetic route is introduced below. Recommanded Product: 3-Amino-4-cyanopyridine

4-Amino-3-(3H-imidazo[4,5-b]pyridin-2-yl)-1,7-naphthyridin-2(1H)-one LiHMDS (3.0 eq) was added to ethyl 3H-imidazo[4,5-b]pyridin-2-ylacetate (1.0 eq) in THF at -78 C. After 20 minutes, a solution of 3-aminopyridine-4-carbonitrile (1.1 eq) in THF was added. The resulting mixture was allowed to warm to room temperature, stirred 3 hours, and then refluxed overnight. The mixture was cooled to 0 C. and quenched with an aqueous saturated NH4Cl solution. A precipitate formed, was filtered off, and was washed repeatedly with ether to yield the desired compound as a brown solid. Purification by reverse phase chromatography afforded the desired product as a yellow solid. LC/MS m/z 279.0 (MH+), Rt 1.29 minutes.

The synthetic route of 78790-79-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Renhowe, Paul A.; Machajewski, Timothy; Shafer, Cynthia M.; Wernette-Hammond, Mary Ellen; Pecchi, Sabina; US2002/103230; (2002); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 17228-75-0, 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. 17228-75-0, name is 2,6-Dichloro-4-methoxypyridine. A new synthetic method of this compound is introduced below.

To a solution of 2,6-dichloro-4-methoxypyridine (18.1 g, 102 mmol) in sulfuric acid (110 mL) was added nitric acid (15.6 mL) dropwise at 0 C., and then the mixture was heated to 100 C. for 2 hours. The reaction mixture was poured into ice-water, the suspension was filtered and washed with water to obtain 2,6-dichloro-4-methoxy-3-nitropyridine as a white solid (19.9 g, 88% yield). MS (ESI) calcd for C6H4Cl2N2O3: 221.96.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,17228-75-0, 2,6-Dichloro-4-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; BLUM, Charles A.; Caldwell, Richard Dana; Casaubon, Rebecca; Disch, Jeremy S.; Fox, Ryan Michael; Koppetsch, Karsten; Miller, William Henry; NG, Pui Yee; Oalmann, Christopher; Perni, Robert B.; Szczepankiewicz, Bruce G.; White, Brian; US2015/152108; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem