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. 86873-60-1, name is 5-Chloro-2-picolinic acid. This compound has unique chemical properties. The synthetic route is as follows. Safety of 5-Chloro-2-picolinic acid

B. 5-Chloropyridine-2-carbonyl chloride To a dry 250 mL round-bottom flask equipped with magnetic stirrer and reflux condenser was charged 5 g of 5-chloropyridine-2-carboxylic acid (0.0317 mol), 100 mL methylene chloride, and 5 drops of DMF as a catalyst. Some of the solid did not dissolve. Thionyl chloride (10 mL; 0.137 mol) was added in one portion, and the reaction was refluxed for a total of 7 hours. After cooling, the reaction was stripped to dryness and 5.1 g of a white solid was isolated. The NMR data is as follows: 300 MHz 1H NMR (CDCl3, TMS=0 ppm) 1.25 (t, 3H); 1.48 (s, 18H); 2.05 (d, 2H); 3.65 (t, 1H); 4.15 (q, 2H). The sample was stored in the refrigerator and had 59% isolated yield. The sample was used without additional purification and had 91% isolated 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, 86873-60-1, 5-Chloro-2-picolinic acid.

Reference:
Patent; DOW AGROSCIENCES LLC; US2009/253708; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 5435-54-1, 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. 5435-54-1, name is 3-Nitropyridin-4-ol. A new synthetic method of this compound is introduced below.

a) 4-Chloro-3-nitropyridine Phosphorus oxychloride (25 ml, 0.27 mol) was added to 4-hydroxy-3-nitropyridine (7.0 g, 50.0 mmol), followed by reaction at 80 to 90 C. for 1.5 hours. Phosphorus oxychloride was removed by distillation. About 100 g of ice was added to the residue, and 28% aqueous ammonia was added dropwise thereto to adjust the pH to 7. Then, 100 ml of water was added thereto, and the aqueous mixture was extracted three times with 200 ml of dichloromethane. The resulting dichloromethane layer was dried, and then dichloromethane was removed by distillation under reduced pressure to obtain 7.75 g of a yellow liquid (yield: 97.8%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,5435-54-1, 3-Nitropyridin-4-ol, and friends who are interested can also refer to it.

Reference:
Patent; The Green Cross Corporation; US5262415; (1993); A;,
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. 73583-37-6, name is 4-Bromo-2-chloropyridine. A new synthetic method of this compound is introduced below., SDS of cas: 73583-37-6

The compound obtained in Step 1 670 mg (2.03 mmol) to 10 ml of 1,4-dioxane was dissolved in then PdCl2 (dppf) 2.CH2Cl2 163 mg (0.20 mmol) and 4-bromo-2-chloropyridine 1.16 g (6.09 mmol), 2M- sodium carbonate (Na2CO3) aqueous solution was added to 3.05 ml (6.09 mmol) was stirred under reflux at 110 for 4 hours. Celite (celite), filtered and concentrated under reduced pressure the filtrate was purified by silica gel column chromatography (dichloromethane: methanol = 3: 1, v / v) 380 to yield a target compound as a yellow solid in a yield of 60% mg (1.20 gained mmol)

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, 73583-37-6, 4-Bromo-2-chloropyridine.

Reference:
Patent; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; LEE, KYU YANG; IM, JAE CHO; LEE, BYUNG HO; OH, KWANG SEOK; KIM, JEONG YEONG; OH, SEUNG AE; LEE, JEONG HYUN; (38 pag.)KR2015/117319; (2015); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 50735-34-7, Adding some certain compound to certain chemical reactions, such as: 50735-34-7, name is Methyl 2-amino-5-bromopyridine-3-carboxylate,molecular formula is C7H7BrN2O2, 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 50735-34-7.

A mixture of methyl 2-amino-5-bromonicotinate (1 g, 4.33 mmol), 4,4,4′,4′,5,5,5′,5′- octamethyl-2,2′-bi(1,3,2-dioxaborolane) (1.319 g, 5.19 mmol), potassium acetate (1.274 g, 12.98 mmol) in dioxane (20 mL) was degassed (3 x) with vacuum/nitrogen.1,1′- Bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (0.353 g, 0.433 mmol) was added, and the mixture was degassed (2 x) and filled with N2. The reaction mixture was immersed in an oil bath at 80 C and stirred ON. The mixture was diluted with ethyl acetate, and washed with water and brine. The organic layer was collected, and the aqueous layers were sequentially extracted with ethyl acetate (2 x). The combined organic layers were dried over anhydrous sodium sulfate and concentrated. After purification by Biotage flash chromatography (40 g column; 0% – 100% ethyl acetate in hexane), the obtained product was triturated with ether to afford methyl 2- amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinate (0.6 g, 2.157 mmol, 49.8 % yield) as a light tan solid. (0645) MS ESI m/z 279.18 (M+H)

According to the analysis of related databases, 50735-34-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WATTERSON, Scott Hunter; ANDAPPAN MURUGAIAH SUBBAIAH, Murugaiah; DZIERBA, Carolyn Diane; GONG, Hua; GUERNON, Jason M.; GUO, Junqing; HART, Amy C.; LUO, Guanglin; MACOR, John E.; PITTS, William J.; SHI, Jianliang; VENABLES, Brian Lee; WEIGELT, Carolyn A.; WU, Yong-Jin; ZHENG, Zhizhen Barbara; SIT, Sing-Yuen; CHEN, Jie; (810 pag.)WO2019/147782; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 98549-88-3, 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.98549-88-3, name is 1H-Pyrrolo[2,3-b]pyridin-5-ol, molecular formula is C7H6N2O, molecular weight is 134.14, as common compound, the synthetic route is as follows.

1H-pyrrolo [2,3-b] pyridin-5-ol(1.20 g, 8.95 mmol, 1.03 eq) and methyl 2,4-difluorobenzoate (1.5 g, 8.71 mmol, 1.0 eq) were added to 20 mL of diethylene glycol dimethyl ether, followed by addition of potassium phosphate heptahydrate (3.5 G,14.0 mmol, 1.6 eq) under nitrogen atmosphere at 115 C overnight. TLC point plate analysis, as well as raw materials, most of which produce ortho products. TLC point plate analysis, as well as raw materials, add 0.3g 2,4-difluorobenzoic acid methyl ester and 0.5g potassium phosphate heptahydrate, continue to react overnight. And then TLC point board analysis, the effect is not very good, as well as raw materials. (30 mL × 3), the organic phase was dried with anhydrous sodium sulfate, spin-dried column, PE / EA (v / v) = 3/1 column, white Solid 525mg. Yield 22.2%.

Statistics shows that 98549-88-3 is playing an increasingly important role. we look forward to future research findings about 1H-Pyrrolo[2,3-b]pyridin-5-ol.

Reference:
Patent; Sunshine Lake Pharma Co.,Ltd.; Kou, Yuhui; Hu, Bolin; Jiang, Haigang; Ye, Jiuyong; Liu, Zhiqiang; Xie, Hongming; Zhang, Yingjun; (42 pag.)CN106565706; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 13534-98-0 , The common heterocyclic compound, 13534-98-0, name is 4-Amino-3-bromopyridine, molecular formula is C5H5BrN2, 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 solution of intermediate 2 (1.12 g, 5.34 mmol), 4-amino-3-bromopyridine (0.924 g, 5.34 mmol), copper (I) iodide (102 mg, 0.534 mmol), triethylamine (3.59 mL, 25.8 mmol) and PdCl2(PPh3)2 (187 mg, 0.267 mmol) in DMF (9.24 mL) was purged by bubbling nitrogen. The mixture was stirred at 100 C overnight under N2. The mixture was cooled to rt and filtered through celite and the filtrate was kept. The celite plug was washed with EtOAc and the combined filtrates were washed with brine (3x), dried over MgS04, filtered and the volatiles were evaporated in vacuo. The crude material was purified on a 24 g Si02 gold column (elution with 0-5%> MeOH containing 2M NH3 over 7 min). The desired fractions were concentrated in vacuo to yield intermediate 6 as a light yellow solid (330 mg, 20%> yield).

The synthetic route of 13534-98-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BARTOLOME-NEBREDA, Jose, Manuel; TRABANCO-SUAREZ, Andres, Avelino; MARTINEZ VITURRO, Carlos, Manuel; TRESADERN, Gary, John; ALCAZAR-VACA, Manuel, Jesus; (126 pag.)WO2018/109198; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 17282-04-1, 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. 17282-04-1, name is 2-Chloro-3-fluoropyridine, molecular formula is C5H3ClFN, 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 flask was charged with 2-chloro-3-fluoropyridine (1.163 g, 8.84 mmol) and THF (15 mL). The mixture was cooled to -78 C and then a solution of n-butyl lithium BuLi (2.83 ml, 7.07 mmol) in tolune solution was added dropwise. The mixture was aged at -78 C for 30 min, and a solution of (6R,8aS)-N-methoxy-N-methyl-3- oxooctahydroindolizine-6-carboxamide (1.0 g, 4.42 mmol) in THF ( 2.5 mL) was added dropwise by syringe. The resulting reaction mixture was stirred at -78 C for 2 hrs. The mixture was quenched with water at low temperature, extracted with EtOAc 3x, dried over MgS04, filtered and concentrated in vacuo to give crude. Crude was loaded and purified on 24 gr Redi Sep Rf filter column on CombiFlash with 10% MeOH/DCM 0- 3% to afford product (6R,8aS)-6-(2-chloro-3-fluoroisonicotinoyl)hexahydroindolizin- 3(2H)-one LC-MS (ES, m/z) Ci4H14ClF 202: 296; Found 297[M+H]+.

According to the analysis of related databases, 17282-04-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LIU, Jian; KIM, Ronald, M.; KOZLOWSKI, Joseph; KRIKORIAN, Arto, D.; ANAND, Rajan; WO2015/95099; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 77992-44-0, 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 77992-44-0 as follows.

A mixture of [5-BROMO-PYRIDINE-2-YL-HYDRAZINE] (4.34 g, 23.1 [MMOL)] and isobutyryl chloride (21.8 mL, 0.208 mol) is [REFLUXED] gently for 3 hours. The mixture is cooled to room temperature. Hexane (22.0 mL) is added and the slurry is stirred at room temperature for 15 minutes and filtered. The cake is washed with hexane (3x) and dried in a vacuum-oven (30- [35C)] for 48 hours. The product (5.90 [G,] yield 92.3%) is obtained as an off-white powder. A biphasic mixture of the product (5.87 [G,] 21.2 [MMOL),] water (12.0 mL) and dichloromethane (18.0 mL) is cooled to 5-10 [C.] A [1N] aqueous solution of [NAOH] (21.5 mL) is added over a period of 10 minutes. The mixture is stirred in the bath for 15 minutes. The organic layer is isolated and the aqueous layer extracted with dichloromethane (2x). The combined organic extracts are washed with 1: 1 brine-water and dried [(MGS04). MOST] of the dichloromethane is removed in vacuo. Ethyl acetate (8.0 mL) is added. After removing about half of the solvents, hexane is added. The slurry is stirred in an ice-water bath for 2 hours and filtered. The cake is washed with 9: 1 hexane-Ethyl acetate (3x) and dried in a vacuum-oven [(30-35C)] for 18 hours. The title compound may be obtained as a sandy tan powder (4.72g, 92.5%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,77992-44-0, its application will become more common.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2004/20440; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 52605-98-8, 5-Bromo-2,3-dimethoxypyridine, 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, Computed Properties of C7H8BrNO2, blongs to pyridine-derivatives compound. Computed Properties of C7H8BrNO2

Add 2,3-dimethoxy-5-bromopyridine (218mg, 1.0mmol) to 5mL N, N-dimethylformamide solution, add cuprous cyanide (179.2mg, 4.0mmol), protect with argon Then, the temperature was raised to 160 C, and the reaction was completed after 8 hours of reaction. Cooled to room temperature, diluted with water, extracted with ethyl acetate, washed with saturated brine, dried over anhydrous sodium sulfate, concentrated to remove the solvent, and column chromatography (petroleum ether: ethyl acetate = 10: 1) to obtain the product 2,3- Dimethoxy-5-cyanopyridine (i.e. compound 16, 164.2 mg, 1.0 mmol), white solid, yield 50%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,52605-98-8, 5-Bromo-2,3-dimethoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; Zhiyuan Pharmaceutical (Qingyuan) Co., Ltd.; Wu Deyan; Xie Ying; Zhou Huifang; (24 pag.)CN110498784; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 6000-50-6, 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. 6000-50-6, name is 2,3-Dihydro-1H-pyrrolo[3,4-c]pyridine dihydrochloride. A new synthetic method of this compound is introduced below.

To a solution Intermediate 106 (500 mg, 1.34 minol) in THE (15 mL) was added at r.t. 4- nitrophenylchloroformate (270 mg, 1.34 minol) and the mixture stirred for 14 h at that temperature. After concentrating the mixture under reduced pressure the residue was taken upin dichloromethane (40 mL) and N,N-diisopropylethyl amine (0.78 mL, 4.4 minol) and 2,3- dihydro-1 H-pyrrolo[3,4-c]pyridine dihydrochloride (274 mg, 1 .42 minol) were added. The reaction mixture was heated to 6000 for 4h and then poured on water. After basification of the mixture with I N aqueous sodium hydroxide solution the mixture was extracted with dichloromethane (2x). The combined organic extracts were washed with brine and filtered through a phaseseparator filter. The residue on the filter was dried at 50°C under vacuum to give the titlecompound (446 mg, 1.03 minol, 72percent).1H-NMR (400 MHz, DMSO-d6): 6 [ppm] = 8.77 (s, IH), 8.71 (s, IH), 8.65 (d, IH), 7.76-7.64 (m,5H), 4.95-4.86 (m, 4H), 3.80 (br t, 2H), 3.60 (t, 2H), 2.84 (s, 2H), 1.09 (s, 6H).LC-MS (Method 6): Rt = 0.79 min; MS (ESIpos): mz = 408 [M÷H].

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6000-50-6, 2,3-Dihydro-1H-pyrrolo[3,4-c]pyridine dihydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; GIESE, Anja; QUANZ-SCHOEFFEL, Maria; MUeLLER, Thomas; GUeNTHER, Judith; BOeHNKE, Niels; GRIEBENOW, Nils; BARAK, Naomi; BOeMER, Ulf; NEUHAUS, Roland; OSMERS, Maren; KOPITZ, Charlotte Christine; KAULFUSS, Stefan; REHWINKEL, Hartmut; WEISKE, Joerg; BADER, Benjamin; CHRISTIAN, Sven; HILLIG, Roman; (426 pag.)WO2018/86703; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem