Pyridine-derivatives

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. 77332-89-9, name is 3-Chloro-2-iodopyridine, the common compound, a new synthetic route is introduced below. Recommanded Product: 77332-89-9

3-Chloro-2-iodopyridine (1.552 g, 6.482 mmol), isobutylboronic acid (0.725 g, 7.112 mmol), potassium carbonate (2.7 g, 0.0195 mol) and silver oxide (3.8 g, 0.0164 mol) were suspended in THF (25 mL). The mixture was degassed three times and 1,1-Bis(diphenylphosphino)ferrocene-palladium(11)dichloride dichloromethane (1:1) (0.520 g, 0.637 mmol) was added. The reaction mixture was heated at 75 C. under nitrogen for seven hours. The mixture was diluted EtOAc (15 mL) and washed with an aqueous solution of hydrochloric acid (2.0 M, 2×15 mL). The organic layer was discarded and the aqueous layer basified with careful addition of a saturated aqueous solution of sodium hydrogen carbonate (50 mL). The product was extracted with EtOAc (2×15 mL). The organics were combined, dried over sodium sulfate, filtered, and concentrated in vacuo. The resulting crude was purified by silica gel chromatography eluting with 0 to 5% EtOAc in heptane to yield the title compound as a colourless oil (0.582 g, 53% yield).1H NMR (400 MHz, d6-DMSO): delta 0.87-0.89 (d, 6H), 2.09-2.17 (m, 1H), 2.72-2.74 (d, 2H), 7.24-7.27 (m, 1H), 7.83-7.86 (m, 1H), 8.44-8.45 (m, 1H).LCMS Rt=1.30 minutes MS m/z 170 [MH]+

The synthetic route of 77332-89-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER LIMITED; US2012/10183; (2012); 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

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

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

Related Products of 571189-16-7, 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. 571189-16-7, name is tert-Butyl 4-(6-nitropyridin-3-yl)piperazine-1-carboxylate, molecular formula is C14H20N4O4, 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.

1-tert-Butoxycarbonyl-4-(6-nitro-3-pyridyl)pyridazine (9.8 g, 31.78 mmol), ferric chloride hexahydrate added in a 250 mL three-neck round bottom flask at room temperature (0.6 g, 2.22 mmol) activated carbon (1.77 g) and ethanol(150mL), heat up to 80 C for 0.5h, cool down to 65 C, slowly add hydrazine hydrate (4.5mL, 73.9mmol), continue to heat upThe reaction was stirred at 80 C for 14 h, filtered while hot, washed three times with ethanol, most of the ethanol was removed under reduced pressure, and a yellow solid was evaporated.Filtration, drying and recrystallization from ethanol gave yellow acicular solid 1-tert-butoxycarbonyl-4-(6-amino-3-pyridyl)pyridazine8.617 g, yield 97.4%, purity 98.8%.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 571189-16-7, tert-Butyl 4-(6-nitropyridin-3-yl)piperazine-1-carboxylate.

Reference:
Patent; Hubei University; Ren Jiaqiang; Zhang Jianxin; Chen Qi; Li Linglan; Chen Yong; (15 pag.)CN108822026; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1207758-80-2, 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. 1207758-80-2, name is 3-(5-Bromo-2-pyridyl)-3-oxetanol, molecular formula is C8H8BrNO2, 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.

A mixture of sodium carbonate (0.54 g, 5.08 mmol) dissolved in water (2.5 mL, 140 mmol) and 1,4-dioxane (6.10 mL, 78.2 mmol) is sonicated for 5 minutes then degassed with bubbling N2 for 15 min. The product of step 1-Example 8 (0.300 g, 1.30 mmol) and step 4-Example 8 (0.647 g, 1.56 mmol) are added successively. After addition, [1,1?-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.0668 g, 0.0913 mmol) is added and the reaction mixture heated at 60 C. for 2 hours before being cooled to room temperature and diluted with ethylacetate. The mixture is washed with water (20 mL), followed by brine (20 mL), dried over MgSO4 and the solvent removed under reduced pressure. The crude material is purified by chromatography eluting neat heptanes to 70% ethylacetate in hexanes to give the title compound (410 mg): m/z (CI) M+H 437.

According to the analysis of related databases, 1207758-80-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ZOETIS LLC; Billen, Denis; Curtis, Michael; Ewin, Richard Andrew; Goodwin, Richard M.; Johnson, Paul D.; Johnson, Timothy Allan; Kyne, Graham M.; Maddux, Todd M.; Sheehan, Susan Mary Kult; Vairagoundar, Rajendran; US2014/88046; (2014); 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

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

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