Month: September 2021

Electric Literature of 72587-15-6, Adding some certain compound to certain chemical reactions, such as: 72587-15-6, name is 2-Chloro-3-nitro-5-(trifluoromethyl)pyridine,molecular formula is C6H2ClF3N2O2, 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 72587-15-6.

A microwave reaction vial was charged with 2-chloro-3-nitro-5-(trifluoromethyl)pyridine (2 g, 8.83 mmol), NMP (4.41 ml) and CuCN (0.830 g, 9.27 mmol). The vial was sealed and the mixture was irradiated in the MW at 175 C. for 15 min. Upon cooling to RT, the reaction mixture was poured onto ice and EtOAc was added. The mixture was filtered through Celite, washing with EtOAc and a small amount of MeOH. The layers of the filtrate were separated, and the aqueous portion was extracted again with EtOAc. The combined organic portions were dried with sodium sulfate, filtered and concentrated. The crude material was purified by silica gel chromatography, using a gradient of 0-30% EtOAc in heptane to provide 3-nitro-5-(trifluoromethyl)picolinonitrile (645 mg, 2.97 mmol, 33.7% yield) as a yellow oil that solidified upon standing. LC/MS (ESI) m/z=218.1 (M+H)

According to the analysis of related databases, 72587-15-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; WHITE, Ryan; ALLEN, Jennifer R.; EPSTEIN, Oleg; HONG, Fang-Tsao; HUA, Zihao; HUMAN, Jason Brooks; LOPEZ, Patricia; OLIVIERI, Philip R.; ROMERO, Karina; SCHENKEL, Laurie; STELLWAGEN, John; TAMAYO, Nuria A.; ZHENG, Xiao Mei; US2014/213581; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1073182-59-8 ,Some common heterocyclic compound, 1073182-59-8, molecular formula is C7H7ClN2O2, 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 stirring suspension of methyl 5-amino-2-chloroisonicotinate (200 mg, 1.07 mmol) and 6-fluoro-2-naphthoic acid (245 mg, 1.29 mmol) in DCM (10.7 rriL) was added dropwise methanesulfonyl chloride (0.124 mL, 1.61 mmol). Hunigs base (0.560 rriL, 3.22 mmol) was then added, followed by DMAP (13.1 mg, 0.107 mmol) and the resulting solution was stirred at rt overnight. The solvent was evaporated in vacuo and the residue then re-suspended in DCM and ether. The precipitate was collected via vacuum filtration, washed with ether to furnish the desired material.

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. 1073182-59-8, Methyl 5-amino-2-chloroisonicotinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; INCEPTION 1, INC.; JACINTHO, Jason, Duarte; CLARK, Ryan, Christopher; SHENG, Tao; OBALLA, Renata, Marcella; STOCK, Nicholas, Simon; ROPPE, Jeffrey, Roger; (161 pag.)WO2017/192304; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 156094-64-3, 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.156094-64-3, name is 3-Bromo-2-(bromomethyl)-6-methoxypyridine, molecular formula is C7H7Br2NO, molecular weight is 280.9446, as common compound, the synthetic route is as follows.

A mixture of 3-bromo-2-(bromomethyl)-6-methoxypyridine (1.4 g, 5.0 mmol), methyl 3-iodo-4-hydroxybenzoate (1.52 g, 5.5 mmol), potassium phosphate (1.6 mg, 7.5 mmol) in DMF (10 mL) was stirred at 60 C for 3 h. Then the reaction mixture was cooled to rt, diluted with water (40 mL), extracted with EA (80 mLx2). The combined organic layers were washed with saturated brine (20 mL), dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by column chromatography eluted with PE/EA (v/v = 20/1) to give the title compound as a white solid (2.2 g, 92 %).MS (ESI, pos. ion) m/z: 477.9 [M+H]t

The chemical industry reduces the impact on the environment during synthesis 156094-64-3, I believe this compound will play a more active role in future production and life.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; WANG, Xiaojun; YANG, Xinye; WU, Junwen; XIONG, Shaohui; PAN, Shengqiang; CAO, Shengtian; ZHANG, Yingjun; (121 pag.)WO2018/24224; (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. 66521-66-2, name is 4-(Pyridin-3-yl)pyrimidin-2-amine, the common compound, a new synthetic route is introduced below. Recommanded Product: 4-(Pyridin-3-yl)pyrimidin-2-amine

General procedure: Reactions were carried out with 4-(pyridin-3-yl)pyrimidin-2-amine 1 (0.50 mmol), aldehyde 2 (0.50 mmol) and malonate 3 (5 mmol) in the presence of catalyst III or IV (10 molpercent) at 50 °C and stirred for 48h. After completion of the reaction (as observed by TLC), the crude product was purified by preparative TLC (GF254 silica gel: hexane/EtOAc = 7/1), giving the target chiral product

The synthetic route of 66521-66-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bai, Song; Liu, Shan; Zhu, Yunying; Lu, Jiali; Ai, Lina; Xue, Jing; Wu, Qin; Journal of Chemical Research; vol. 42; 8; (2018); p. 428 – 433;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 130721-78-7, 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 130721-78-7, name is tert-Butyl (4-chloropyridin-2-yl)carbamate. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a – 78Csolution of N-Boc-2-amino-4-chloropyridine(3.6g, 15.8 mmol) and TMEDA (3.7 g, 31.2 mmol) in anhydrous THF (67 mL) wasadded dropwise a 1.3 M solution of n-BuLiin hexane (25 mL, 31.2 mmol). The reaction mixture was stirred at -78C during 1hand then a solution of I2 (8.0 g, 31.2 mmol) inTHF (27 mL) was added dropwise. Temperature was allowed to rise at roomtemperature during 1h and the reaction mixure was hydrolized with a saturatedsolution of ammonium chloride (30 mL) and extracted with EtOAc (3 x 30 mL). Thecombined organic phases were washed with a 10% solution of Na2S2O3(30 mL), brine (30 mL), dried over MgSO4, filtered and concentrated under reduced pressure. The iodinated aminopyridine was obtained as a beigesolid (4.2 g, 76%) without further purification.

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 130721-78-7, tert-Butyl (4-chloropyridin-2-yl)carbamate.

Reference:
Article; Silpa, Laurence; Niepceron, Alisson; Laurent, Fabrice; Brossier, Fabien; Penichon, Melanie; Enguehard-Gueiffier, Cecile; Abarbri, Mohamed; Silvestre, Anne; Petrignet, Julien; Bioorganic and Medicinal Chemistry Letters; vol. 26; 1; (2016); p. 114 – 120;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 66909-30-6, 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 66909-30-6 as follows.

6-(4-(2-Chloro-5-methylnicotinamido)benzoyl)-W-(2-fluoro-6-methylphenyl)-5,6-di hydro-4H-benzo[i)]thieno[2,3-c ]azepine-2-carboxamide; Intermediate (Ilia). Oxalyl chloride (133 mL, 1.58 mol) was added to a suspension of 2-chloro-5-methyl nicotinic acid (225.4 g, 1.313 mol) in DCM (2254 mL) at 18-25C followed by DMF (0.8 mL, 0.010 mol) (results in mild exotherm and gas evolution) and the reaction stirred at 20-25C for 1 hr. HPLC analysis of an aliquot (quenched into methanol) indicated <1 % of 2-chloro-5- methylnicotinic acid was remaining. The solvent was removed in vacuo and the oily residue was azeotroped with DCM (500 mL) to remove residual oxalyl chloride. The resulting oil was taken up into DCM (413 mL) and was added dropwise over 10 min to a suspension of 6-(4-aminobenzoyl)-/V-(2-fluoro-6-methylphenyl)-5,6-dihydro-4/-/-benzo[ 5] thieno[2,3-d]azepine-2-carboxamide (412.9 g, 0.876 mol) in a mixture of pyridine (283 mL, 3.502 mol) and DCM (28920 mL) whilst maintaining the internal temp <40C (maximum temp reached 38C). The reaction was stirred at 18-25C for 1 hr after which time HPLC (sample quenched into methanol) indicated the reaction was complete (<1 % of aniline s/m remaining). Heptane (3300 mL) was added to the mixture at 18-25C and the resulting suspension was stirred for 15 min and the solids then collected by filtration. The filter cake was washed with heptane (2 x 1650 mL) and the crude solid so obtained was slurried in water (4130 mL) at 90- 95C for 30 min and then cooled to 18-25C.The solids were collected by filtration, washed with water (2 x 826 mL) and dried in a vacuum oven at 50C to give the title compound as a white solid (504.2 g, 92% active yield, HPLC purity [230 nm] 98.24%; containing 0.3% pyridine HCI by 1 H NMR and 0.4%. H20 by KF); R< 12.19 min; m/z 625.6 (M+H)+ (ES+). These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,66909-30-6, its application will become more common. Reference:
Patent; PULMOCIDE LIMITED; HUNT, Simon Fraser; ONIONS, Stuart Thomas; SHERBUKHIN, Vladimir; FORDYCE, Euan Alexander Fraser; MURRAY, Peter John; BROOKES, Daniel William; ITO, Kazuhiro; STRONG, Peter; (51 pag.)WO2016/55791; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 15862-37-0, 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. 15862-37-0, name is 2,5-Dibromo-3-nitropyridine, molecular formula is C5H2Br2N2O2, 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.

B. (7-BROMO-PYRIDO [3, 2-D] PYRIMIDIN-4-YL-4-TERT-BUTYL-ISOXAZOLE)-AMINE (COMPOUND 2) 1. 5-bromo-3-nitropyridine-2-carbonitrile Heat a solution of 2, 5-dibromo-3-nitropyridine (1.77g, 6.3 mmol; Malinowski (1988) Bull. Soc. Chim. Belg 97 : 51 ; see also US 5, 801, 183) and cuprous cyanide (0.60 g, 6.69 mmol) in N, N-dimethylacetamide (25 mL) at 100C for 72 hours. After cooling, dilute the mixture with water (25 mL) and extract twice with EtOAc (25 mL each), then wash twice with water (25 mL each). The combined EtOAc extracts are dried (Na2SO4), evaporated, and purified by flash chromatography (50% EtOAc-hexane) to obtain 5-bromo-3-nitropyridine-2- carbonitrile as a pale solid.

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 15862-37-0, 2,5-Dibromo-3-nitropyridine.

Reference:
Patent; NEUROGEN CORPORATION; WO2005/42498; (2005); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 909036-46-0, 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 909036-46-0, name is 2-Chloro-3-iodopyridin-4-amine. This compound has unique chemical properties. The synthetic route is as follows.

Into a 250 mL round bottom flask was placed the 2-chloro-3-iodo-4-aminopyridine (3.0 g, 11.8 mmol), thiophenol (1.3 g, 11.8 mmol), copper(I) iodide (0.11 g, 0.58 mmol), ethylene glycol (1.5 g, 24 mmol) and potassium carbonate (3.3 g, 24 mol). 100 mL of 2-propanol was then added to the reaction mixture and the mixture was heated at reflux for 18 h. The reaction mixture was cooled to room temperature and was filtered under vacuum. The filtrate was diluted with 200 mL of water then was extracted two times with 150 mL of ethyl acetate. The extracts were dried over magnesium sulfate then were filtered and stripped under vacuum. The product was purified using Silica gel chromatography with 2-15% ethyl acetate/dichloromethane as the mobile phase. 2.0 g (72% yield of product was collected.

According to the analysis of related databases, 909036-46-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Universal Display Corporation; Rayabarapu, Dinesh; Xia, Chuanjun; Kwong, Raymond; Ma, Bin; Yeager, Walter; Alleyne, Bert; (82 pag.)CN102449107; (2016); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 885276-93-7, 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. 885276-93-7, name is Ethyl 5-bromopyrazolo[1,5-a]pyridine-3-carboxylate, molecular formula is C10H9BrN2O2, 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.

General procedure: These were made by decarboxylation/Vilsmeier or hydrolysis/reduction/reoxidation as detailed below, unless otherwise stated.Decarboxylation was carried out by refluxing a solution of the ester (1 equiv) in 40% aqueous H2SO4 (3 mL) for 18 h. The solution was then cooled in ice and neutralised to pH 7 with 6 M NaOH, then extracted twice with CH2Cl2. The combined extracts were dried (Na2SO4) and the solvent removed in vacuo to leave the decarboxylated material. The pyrazolo[1,5-a]pyridine was then reacted under Vilsmeier conditions in dry DMF (2 mL) with POCl3 (3 equiv) at 0 C under an atmosphere of N2. The reaction mixture was then warmed to room temperature and stirred for 2 h. The solution was poured onto ice, basified to pH 10 with 1 M NaOH, stirred for 1 h then extracted twice with CH2Cl2. The combined extracts were washed twice with water, dried (Na2SO4) and the solvent removed in vacuo to leave the aldehyde.Alternatively, the ester was hydrolysed by refluxing a solution of the ester (1 equiv) in 1 M NaOH (3 equiv) and EtOH (5 mL) for 6 h. The EtOH was removed in vacuo, and then the aqueous residue acidified to pH 1 with 1 M HCl. The precipitated carboxylic acid was filtered off, washed with water and dried. The carboxylic acid was reduced by adding CDI (1.5 equiv) to a suspension of carboxylic acid (1 equiv) in dry THF (10 mL) under an atmosphere of N2. After stirring for 18 h, the resulting solution was added dropwise to a solution of NaBH4 (5 equiv) in H2O (10 mL) and stirred for 30 min. The reaction was then quenched by the addition of 1 M HCl and stirred for a further 30 min. The solution was neutralised with saturated aqueous NaHCO3 and extracted twice with CH2Cl2. The combined organic layers were dried (Na2SO4) and the solvent removed in vacuo. Chromatography (eluting with a hexanes: EtOAc gradient) gave the alcohol. Reoxidation was carried out by stirring a suspension of the pyrazolo[1,5-a]pyridine-3-methanol (1 equiv) and MnO2 (10 equiv) in CH2Cl2 (2 mL) at room temperature for 4 days. The reaction mixture was then filtered through celite, washed with CH2Cl2, and the solvent removed from the filtrate in vacuo to leave the aldehyde.

According to the analysis of related databases, 885276-93-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kendall, Jackie D.; O’Connor, Patrick D.; Marshall, Andrew J.; Frederick, Raphael; Marshall, Elaine S.; Lill, Claire L.; Lee, Woo-Jeong; Kolekar, Sharada; Chao, Mindy; Malik, Alisha; Yu, Shuqiao; Chaussade, Claire; Buchanan, Christina; Rewcastle, Gordon W.; Baguley, Bruce C.; Flanagan, Jack U.; Jamieson, Stephen M.F.; Denny, William A.; Shepherd, Peter R.; Bioorganic and Medicinal Chemistry; vol. 20; 1; (2012); p. 69 – 85;,
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. 866319-00-8, name is 5-Fluoro-1H-pyrrolo[2,3-b]pyridine. A new synthetic method of this compound is introduced below., Product Details of 866319-00-8

Dissolve 5-fluoro-1H-pyrrole-[2,3-b]pyridine (35.00 g, 257·1 mmol, 1.0 equiv.) in 200 ml DMF, cool to 0 C, add NaH (60 Wt) in portions. % in mineral oil, 10.80 g, 270.0 mmol, 1.05 equiv.), reacted for 30 min, added triisopropylchlorosilane (54.53 g, 282.8 mmol, 1.1 eq.).After reacting at 0 C for 2 hours, TLC showed the reaction was completed. Quenched by adding 50 ml of water, the system was poured into 1 L of water, 1 L of petroleum ether was added, and the mixture was separated and filtered with silica gel. The mother liquid was concentrated to give 82.10 g of a crude yellow oil.

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, 866319-00-8, 5-Fluoro-1H-pyrrolo[2,3-b]pyridine.

Reference:
Patent; Nanjing He Ju Pharmaceutical Co., Ltd.; Pan Guojun; (7 pag.)CN110016030; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem