Pyridine-derivatives

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 10128-91-3, name is Methyl 2-oxo-1,2-dihydro-3-pyridinecarboxylate. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 10128-91-3

(b) Methyl 2-hydroxy-5-iodonicotinate. A solution of methyl2-hydroxynicotinate (100 g, 0.65 mol) and N-iodosuccinimide (192 g, 0.85 mol) in dry DCM (2.5 L) was heated at reflux in the dark for 48 hours. The mixture was concentrated to 500 mL under reduced pressure. The solid which precipitated was collected by filtration, washed with small portions of cold DCM, and dried in vacuo to give the title compound as a pale-yellow solid.

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Reference:
Patent; AMGEN INC.; WO2008/130600; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 5470-66-6, name is 4-Nitro-2-picoline N-oxide. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C6H6N2O3

A solution OF 2-METHYL-4-NITROPYRIDINE-N-OXIDE (3.80 g, 24.6 mmol) in 100 ML of acetic acid was slowly heated with iron powder (6.89 g, 124 mmol) in a large flask (caution: the reaction becomes very exothermic upon turning brown). The resulting slurry was heated for 2 hours at 80 C. Excess acetic acid was removed IN VACUO, THE residue was taken up in 20% aqueous sodium hydroxide solution, and 100 mL of chloroform (CHC13) was added and the mixture filtered through CELITES FILTER aid. The aqueous phase was extracted with two 200 mL portions of chloroform. The combined organic layers were dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude product (2.2 g, 83% yield) was used without further purification. A solution OF KI (1. 96 g, 11. 9 mmol) and 12 (1.87 g, 7.36 mmol) in 10 ML of water was added to a REFLUXING solution of the 2-methylpyridin-4-ylamine (1.00 g, 9.25 mmol) and sodium carbonate (683 mg, 6.44 mmol) in 5 ML of water. The mixture was heated at reflux for 2 hours, cooled to room temperature, and treated with 20 mL of ethyl acetate (EtOAc). Phases were separated and the aqueous layer was extracted with three 20 ML portions of ethyl acetate. The combined organic layers were washed with a saturated aqueous sodium thiosulfate (NA2S203) solution, dried over magnesium sulfate, and concentrated ILL vacuo. Flash chromatography (30% ethyl acetate in hexanes to 100% ethyl acetate, gradient) of the resulting residue yielded 4-amino-3-iodo-6-methylpyridine (first eluting: 226 mg, 11% yield) and 4- AMINO-3-IODO-2-METHYLPYRIDINE (second eluting : 116 mg; 5% yield).

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, 5470-66-6, 4-Nitro-2-picoline N-oxide.

Reference:
Patent; BOEHRINGER INGELHEIM PHARMACEUTICALS, INC.; WO2005/30213; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1594-58-7 ,Some common heterocyclic compound, 1594-58-7, molecular formula is C6H7N3O, 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.

5-(Chloromethyl)-3-(pyridine-2-yl)-1 ,2,4-oxadiazole (SO2-065): To a solution of N- hydroxypicolinimidamide (0.2g g, 1 .5 mmol) in DCM (20 ml) and chloroacetyl chloride (0.2 g, 1 .8 mmol) at 0 C, diisopropylethylamine (0.23 g, 1 .8 mmol) was added (dropwise). The mixture was warmed up to r.t. and stirred for 24 h. and organic solvent was evaporated and the residue was refluxed overnight in toluene (20 ml_) to complete the cyclization. The product obtained was purified using Si02 chromatography (EtOAc: hexane gradient elution). The required compound SO2-065 (0.24 g, 81 %) was obtained as a white solid.1 H NM R (400 M Hz, CDCI3) delta 8.81 (ddd, J = 4.8, 1 .6, 1 .0 Hz, 1 H), 8.14 (d, J = 7.9 Hz, 1 H), 7.87 (ddd, J = 7.9 Hz, 4.8 , 1 .8 Hz, 1 H), 7.46 (ddd, J = 7.7, 4.8, 1 .2 Hz, 1 H), 4.79 (s, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1594-58-7, its application will become more common.

Reference:
Patent; H. LEE MOFFITT CANCER CENTER AND RESEARCH INSTITUTE, INC.; LAWRENCE, Harshani R.; SEBTI, Said M.; OZCAN, Sevil; WO2012/129564; (2012); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 58584-63-7, 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. 58584-63-7, name is (6-Methoxypyridin-3-yl)methanol. A new synthetic method of this compound is introduced below.

To a solution of 2-methoxy-5-hydroxymethylpyridine (0.71 g, 0.005mole) in DCM (5 mL) at 0 C under N2, was added thionyl chloride (0.7 mL, 0.009 mole) drop wise. The reaction mixture was warmed to RT and stirred for 2 hours. The reaction mixture was diluted with DCM (50 mL) and treated with saturated aqueous sodium bicarbonate (10 mL). Organic layer was washed with water (20 mL), brine solution (20 mL), dried over Na2SC>4 and concentrated under vacuum to obtain the title compound. Yield: 0.58 g; lH – NMR (CDC13, 400 MHz) delta ppm: 3.94 (s, 3H), 4.55 (s, 2H), 6.75 – 6.77 (d, J = 8.5 Hz, 1H), 7.61 – 7.64 (dd, J = 2.2, 8.5 Hz, 1H), 8.14 (s, 1H); Mass (m/z): 158.0 – 160.0 (M+H) +.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,58584-63-7, (6-Methoxypyridin-3-yl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; SUVEN LIFE SCIENCES LIMITED; NIROGI, Ramakrishna; SHINDE, Anil Karbhari; MOHAMMED, Abdul Rasheed; BADANGE, Rajesh Kumar; JAYARAJAN, Pradeep; BHYRAPUNENI, Gopinadh; JASTI, Venkateswarlu; (172 pag.)WO2018/42362; (2018); 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. 170886-13-2, name is 2-(Trifluoromethyl)pyridin-4-ol, the common compound, a new synthetic route is introduced below. COA of Formula: C6H4F3NO

An alternative synthetic procedure is provided: 3,4,5-trifluorobenzaldehyde (1.08 g, 6.74 mmol) was added to a solution of 2-trifluoromethyl)pyridin-4-ol (1 g, 6.13 mmol) and potassium carbonate (1.017 g, 7.36 mmol) in Nu,Nu-dimethylformamide (DMF) (10 mL) under nitrogen with stirring. The reaction mixture was stirred at 100 C for 16 h, cooled to rt, and then diluted with EtOAc (30 mL) and water (30 mL). The organic phase was washed three times with water (30 mL), dried over sodium sulphate, and then concentrated in vacuo to afford the title compound (1.8 g, 97%). LCMS (ESI): m/z 304 [M + H]+; 1.17 min (ret time)

The synthetic route of 170886-13-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; SANG, Yingxia; WAN, Zehong; ZHANG, Qing; WO2014/114694; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 183208-35-7, Adding some certain compound to certain chemical reactions, such as: 183208-35-7, name is 5-Bromo-1H-pyrrolo[2,3-b]pyridine,molecular formula is C7H5BrN2, 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 183208-35-7.

General procedure: To a cold solution of appropriate pyrrolo-pyridines 8a,c,e (2.5 mmol) in anhydrous toluene (25 mL), t-BuOK (0.38 g, 3.4 mmol) and TDA-1 (1 or 2 drops) were added at 0 C. The reaction mixture was stirred at room temperature for 3 h and then MeI (2.5 mmol, 0.2 mL) was added at 0 C. TLC analysis (ethyl acetate) revealed that methylation was complete after 1 h. The solvent was evaporated under reduced pressure. The residue was treated with water, extracted with DCM (3 × 20 mL), dried (Na2SO4), evaporated and purified by column chromatography using DCM/ethyl acetate (9/1) as eluent to give derivatives 8b,d,f [42].

According to the analysis of related databases, 183208-35-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Carbone, Anna; Parrino, Barbara; Vita, Gloria Di; Attanzio, Alessandro; Span, Virginia; Montalbano, Alessandra; Barraja, Paola; Tesoriere, Luisa; Livrea, Maria Antonia; Diana, Patrizia; Cirrincione, Girolamo; Marine Drugs; vol. 13; 1; (2015); p. 460 – 492;,
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Pyridine | C5H5N – PubChem

Electric Literature of 131674-39-0, Adding some certain compound to certain chemical reactions, such as: 131674-39-0, name is 1-(2-Chloropyridin-3-yl)ethanol,molecular formula is C7H8ClNO, 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 131674-39-0.

To a solution of 2-chloropyridine (XXIX) (31.0 kg, 273 mol) in dry THF (275 L) cooled to -78oC under nitrogen was added LDA (113 L, 1220 mol) dropwise while maintaining the temperature at -78oC and stirred for 5 hours. Acetaldehyde (16 L, 463 mol) was then added and the reaction was stirred at -78oC for another 5 hours before warming to 0oC and adding water (310 L) to quench the reaction. The solution was stirred for 50 min and then warmed to room temperature. The solution was extracted 3 x EtOAc (279 L) by adding EtOAc, stirring for 50 min, allowing to stand for 50 min, separating the layers and then repeating twice. The combined EtOAc was concentrated under vacuum to a volume of 300-500 L. To the crude 1-(2-chloropyridin-3- yl)ethanol (XXX) was added DCM (705 L) followed by an aqueous solution of KBr (3.3 Kg, 27.7 mol) dissolved in water (33 L). The solution was cooled to 0oC before adding TEMPO (1.7 Kg, 10.9 mol) and then stirred for 50 min. In a second container, water (980 L) was added followed by KHCO3 (268 Kg, 2677 mol) and 10% aqueous NaClO (233 L, 313 mol). This aqueous mixture was then added dropwise to the TEMPO mixture. This combined mixture was stirred at 0oC for 5 hours. To this mixture was added dropwise Na2S2O3*7H2O (22.5 Kg, 90 mol) in water (107 L) with stirring for 50 min at 0oC. The mixture was allowed to warm to room temperature and the organic phase was separated. The aqueous phase was extracted 2 x DCM (353 L) by adding DCM, stirring for 50 min, allowing to stand for 50 min, separating the layers and then repeating. The combined organic layers were washed with aqueous 25% NaCl (274 L) and concentrated under vacuum to give crude 1-(2-chloropyridin-3-yl)ethanone (XXXI) which was used for the next step without additional purification.

According to the analysis of related databases, 131674-39-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SAMUMED, LLC; KC, Sunil Kumar; MITTAPALLI, Gopi Kumar; CHIRUTA, Chandramouli; HOFILENA, Brian Joseph; (128 pag.)WO2019/241540; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 19798-81-3, name is 6-Bromopyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows. Safety of 6-Bromopyridin-2-amine

Under ice cooling, a solution of 6-bromopyridin-2-amine (10 g, 57.8 mmol) in MeCN (100 mL) was slowly added dropwise to a solution of NBS (10.3 g, 57.8 mmol) in MeCN (200 mL). After dropping, the temperature was maintained for 1 hour. After completion of the reaction, the mixture was concentrated under reduced pressure to 20 mL. 300 mL of EtOAc was added. The organic phase was washed with H2O, saturated NaCl solution, and dried over anhydrous Na2SO4. The solvent was concentrated under reduced pressure to give the product, 14.2 g, 97% yield, as a white solid

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, 19798-81-3, 6-Bromopyridin-2-amine.

Reference:
Patent; Shenzhen Bolijian Pharmaceutical Co., Ltd.; Huang Liye; Liu Yun; Li Tao; Mao Wenjin; Liu Huabin; (28 pag.)CN107778302; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 87394-65-8, 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 87394-65-8, name is 1-(5-Chloro-2-pyridyl)piperazine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Approximately 0.5 mmol of 2 and 0.5 mmol of HATU were dispensed in 24 reaction wells (MiniBlock XT) using a dispensing spatula and funnel. To each well were added 10 mL of anhydrous MeCN, (0.5 mmol) of the appropriate amine in MeCN, and then 0.13 mL of DIPEA (0.75 mmol) through the septa sheet. The reaction block was covered and shaken at room temperature for 180 minutes (TLC monitored). Two grams of silica gel were added to each well and the reaction block was placed on a parallel centrifugal evaporator. After automated flash chromatography, the obtained pure intermediate (0.25 mmol) and 4 mL of formic acid (50%) were dispensed in 24 reaction wells (MiniBlock XT), heated to 70 C and shaken vigorously for 2 h whereupon TLC showed no remaining starting material. Silica gel (1 g) was added to each well and the mixture was evaporated, dried on a parallel centrifugal evaporator and the dry solid was chromatographed to give the desired product.

According to the analysis of related databases, 87394-65-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Moukha-Chafiq, Omar; Reynolds, Robert C.; Nucleosides, nucleotides and nucleic acids; vol. 33; 11; (2014); p. 709 – 729;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 189449-41-0, (4-Chloropyridin-3-yl)methanol, 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, name: (4-Chloropyridin-3-yl)methanol, blongs to pyridine-derivatives compound. name: (4-Chloropyridin-3-yl)methanol

Example 21 3-chloromethyl-4-chloropyridine hydrochloride Thionyl chloride (0.714 mL, 9.78 mmol) was added at room temperature to dry DMF (7 mL). After 30 min the above solution was cannulated into the solution of 3-hydroxymethyl-4-chloropyridine (700 mg, 4.89 mmol) in DMF (3 mL). After 45 min, the product was precipitated by addition of dry ether (100 ml), washed with ether, and dried in vacuum to yield 813 mg (84percent) of the title compound. 1H NMR (CD3 OD) delta 5.00 (s, 2H), 8.31 (d, 1H, J=S), 8.99 (d, 1H, J=5), 9.18 (s, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,189449-41-0, (4-Chloropyridin-3-yl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; Microcide Pharmaceuticals, Inc.; US5859256; (1999); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem