Category: pyridine-derivatives

Adding a certain compound to certain chemical reactions, such as: 10165-86-3, Methyl 6-formylnicotinate, 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, 10165-86-3, blongs to pyridine-derivatives compound. COA of Formula: C8H7NO3

A mixture of methyl 6-formylnicotinate (1.000 g, 6.055 mmol) and 3-chloro-4-fluoroaniline (0.970 g, 6.66 1 mmol) in tetrahydrofuran (50 mL) was stuffed at the room temperature for 30 mm, and treated with sodium triacetoxyborohydride (1.925 g, 9.083 mmol). The reaction mixture was stuffed at the same temperature for additional 18 hr. Then, saturated aqueous sodium bicarbonate solution was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with aqueous saturated sodium chloride solution, dried with anhydrous MgSO4, filtered, and concentrated in vacuo. The residue was chromatographed (Si02, 40 g cartridge; ethyl acetate / dichloromethane = 0 percent to 5 percent) to give methyl6-(((3-chloro-4-fluorophenyl)amino)methyl)nicotinate as brown solid (0.510 g, 28.6percent).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,10165-86-3, its application will become more common.

Reference:
Patent; CHONG KUN DANG PHARMACEUTICAL CORP.; LEE, Jaekwang; HAN, Younghue; KIM, Yuntae; CHOI, Daekyu; MIN, Jaeki; BAE, Miseon; YANG, Hyunmo; KIM, Dohoon; (644 pag.)WO2017/18803; (2017); 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. 5345-47-1, name is 2-Aminonicotinic acid, molecular formula is C6H6N2O2, 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. COA of Formula: C6H6N2O2

2-Aminonicotinic acid (10.00 g, 72.40 mmol) was suspended in 40 ml of glacial acetic acid. To this suspension was added dropwise a solution of 4.82 ml (94.12 mmol) of bromine in 20 ml of glacial acetic acid. The mixture was stirred vigorouly at room temperature for 30 min. The formed precipitate was filtered off and washed with glacial acetic acid. The filter cake was collected and crystallized from the boiling methol to afford compound 8 as a white solid (14.5 g, 92% yield). 1H NMR (300 MHz, DMSO-d6) delta 8.30 (d, J = 2.4 Hz, 1H), 8.16 (d, J = 2.4 Hz, 1H); MS (ESI, m/z): 216.8 [M+H]+.

With the rapid development of chemical substances, we look forward to future research findings about 5345-47-1.

Reference:
Article; Zhang, Dengyou; Ai, Jing; Liang, Zhongjie; Li, Chunpu; Peng, Xia; Ji, Yinchun; Jiang, Hualiang; Geng, Meiyu; Luo, Cheng; Liu, Hong; Bioorganic and Medicinal Chemistry; vol. 20; 17; (2012); p. 5169 – 5180;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 17228-69-2, 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. 17228-69-2, name is 2-Chloro-4-methoxypyridine. A new synthetic method of this compound is introduced below.

Ethanolamine (4.0 ml) was added to potassium tert-butoxide (96 ml of a 1M solution in THF) and the reaction was stirred at room temperature for 30 min. 2-Chloro-4- methoxypyridine was added dropwise and the reaction mixture was heated under reflux for 16 h. The reaction mixture was cooled, filtered and evaporated to an oil. This was dissolved in xylene (100 ml) and treated with toluene-4-sulphonic acid (50 mg) and heated under reflux for 16 h. More toluene-4-sulphonic acid (50 mg) was added and the heating was continued for a further 16 h under reflux. The mixture was concentrated, the residue was passed through a pad of silica and eluted with 5% 7M ammonia in methanol/DCM to give the sub-title compound as a brown oil (5.0 g). MS APCI +VE/Z 169 ([M+H]). 1H NMR 300MHz (DMSO-d6) 7.76 (1H, d), 6.33 (1H, t), 6.13-6. 10 (1H, m), 5.99 (1H, m), 3.70 (3H, s), 3.54-3. 47 (2H, m), 3.31-3. 25 (2H, m).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,17228-69-2, 2-Chloro-4-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; WO2004/87666; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 586-95-8 ,Some common heterocyclic compound, 586-95-8, molecular formula is C6H7NO, 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.

(IV) 4-Chloromethylpyridine hydrochloride (19) STR16 4-Hydroxymethylpyridine (18) 54.4 g (0.50 mol) was dissolved in acetonitrile 202 ml. The solution was added dropwise to the mixture of thionyl chloride 65.3 g (0.55 mol) and acetonitrile 109 ml under 50 C. The mixture was stirred at the same temperature for 1 hour, then cooled to room temperature to yield the slurry (quantitative) of the objective (19). 1 H-NMR (DMSO-TMS) delta ppm: 5.09 (s, 2H), 8.09 (d, J=6.6 Hz, 2H), 8.94 (d, J=6.6 Hz, 2H),

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,586-95-8, its application will become more common.

Reference:
Patent; Shionogi & Co., Ltd.; US6057448; (2000); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 164666-68-6, 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. 164666-68-6, name is 6-Chloro-2-methylpyridin-3-amine, molecular formula is C6H7ClN2, 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.

Step 2: 6-Chloro-N-isopropyl-2-methylpyridin-3-amine (45). To a stirred solution of 44 (4.81 g, 33.75 mmol) and acetone (2.74 g, 47.2 mmol) in dichloroethane (60 mL) was added NaBH(OAc)3 (10.713 g, 50.53 mmol) and AcOH (3.44 g, 57.2 mmol) at RT. The reaction was stirred for 16 h followed by dilution with IN NaOH. The aqueous solution was extracted with DCM and the organic layer was washed with water, brine, dried over Na2S04 and concentrated to afford 45 (6.16 g, 98%).

According to the analysis of related databases, 164666-68-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; EXELIXIS, INC.; XU, Wei; (106 pag.)WO2017/4608; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1013648-04-8, 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. 1013648-04-8, name is Methyl 2,6-dichloro-4-methylnicotinate, molecular formula is C8H7Cl2NO2, 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 250 ml flask were added methyl 2,6-dichloro-4-methylnicotinate (4.24 g, 19.268 mmol), N-bromosuccinimide (4.1 g, 23.036 mmol), azobisisobutyronitrile (160 mg, 0.974 mmol) and 50 ml of carbon tetrachloride. The reaction mixture was stirred at 85 C. overnight. The reaction mixture was concentrated to remove carbon tetrachloride, and 50 ml of ethyl acetate was added, which was then washed with 50 ml of brine and 50 ml of water successively. The organic phase was dried over anhydrous sodium sulfate, concentrated to give 6.4 g of methyl 4-(bromomethyl)-2,6-dichloronicotinate as an oil, MS m/z (ESI): 300.1[M+H]+.

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 1013648-04-8, Methyl 2,6-dichloro-4-methylnicotinate.

Reference:
Patent; SHANGHAI HAIYAN PHARMACEUTICAL TECHNOLOGY CO., LTD.; YANGTZE RIVER PHARMACEUTICAL GROUP CO., LTD.; GUO, Shuchun; ZHOU, Fusheng; CHEN, Xiang; ZHAO, Jinzhu; HUANG, Dong; XIE, Jing; QIAO, Changjiang; HE, Wan; ZHANG, Kai; CHEN, Xi; LAN, Jiong; (53 pag.)US2020/48248; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 68618-36-0, 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 68618-36-0, name is 3-Bromo-1H-pyrazolo[3,4-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 3-bromo-1H-pyrazolo[3,4-b]pyridine (200 mg, 1.010 mmol), zinc cyanide (1.0 eq., 121.0 mg, 1.010 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.04 eq., 38.1 mg, 0.040 mmol), 1,1?-bis(diphenylphosphino)feffocene (0.08 eq., 46.6 mg, 0.08 1 mmol) and zinc (0.24 eq., 15.8 mg, 0.242 mmol) were dissolved in degassed N,N-dimethylacetamide (5.0 mL) under inert atmosphere. The reaction was heated to 120 C for 5 hours. The reaction was then diluted withaqueous saturated sodium bicarbonate and extracted 2 times with dichloromethane. The organics were combined, washed with brine, dried with sodium sulfate and concentrated under vacuum. The crude material was crashed out in diethyl ether to afford 93 mg of the title compound (64 %).

According to the analysis of related databases, 68618-36-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BLAQUIERE, Nicole; BURCH, Jason; CASTANEDO, Georgette; FENG, Jianwen A.; HU, Baihua; STABEN, Steven; WU, Guosheng; YUEN, Po-wai; WO2015/25025; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1382486-27-2 ,Some common heterocyclic compound, 1382486-27-2, molecular formula is C10H10BrNO2, 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 stirred solution of l-(5-bromopyridin-2-yl)cyclobutanecarboxylic acid (16.9 g, 66.0 mmol) in i-BuOH (30 mL) was added TEA (17.5 mL, 125 mmol) and DPPA (23.6 g, 86 mmol) at RT. After the addition was finished, the reaction was stirred at 85 C under nitrogen for 18 h. After 18 h the solvent was concentrated in vacuo. The residue was purified via column chromatography (Petroleum ether/ EtOAc =10: 1-2: 1) to afford tert-butyl (l-(5-bromopyridin-2- yl)cyclobutyl)carbamate. MS ESI calc’d. [M + H]+ 327, found 327.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1382486-27-2, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WHITE, Catherine M.; ACHAB, Abdelghani; BHARATHAN, Indu T.; FRADERA, Xavier; HAN, Yongxin; LI, Derun; LIM, Jongwon; LIU, Kun; MCGOWAN, Meredeth Ann; SCIAMMETTA, Nunzio; YU, Wensheng; ZHANG, Hongjun; ZHOU, Hua; (107 pag.)WO2019/74749; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 571189-16-7, tert-Butyl 4-(6-nitropyridin-3-yl)piperazine-1-carboxylate, 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, HPLC of Formula: C14H20N4O4, blongs to pyridine-derivatives compound. HPLC of Formula: C14H20N4O4

EXAMPLE 103C ierf-butyl 4-(6-aminopyridin-3-yl)piperazine-l -carboxy late To a suspension of EXAMPLE 103B (4.5 g, 14.6 mmol) in methanol (100 mL) was added Raney -Nickel (450 mg) and the mixture was stirred at ambient temperature under hydrogen for 4 hours. The catalyst was filtered off and the filtrate was concentrated to give the title compound, which was used in the next step without further purification.

The synthetic route of 571189-16-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBOTT LABORATORIES; ABBOTT LABORATORIES TRADING (SHANGHAI) COMPANY, LTD.; VASUDEVAN, Anil; PENNING, Thomas Dale; CHEN, Huanming; LIANG, Bo; WANG, Shaohui; ZHAO, Zhongqiang; CHAI, Dikun; YANG, Leifu; GAO, Yingxiang; WO2012/97682; (2012); 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. 178876-82-9, name is Methyl 6-amino-5-bromopicolinate. A new synthetic method of this compound is introduced below., Quality Control of Methyl 6-amino-5-bromopicolinate

Preparation 4; Preparation of 3-Oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carboxaldehydea) Methyl 3-oxo-3,4-dihydro-2H-pyrido[3.2-b][1,4]thiazine-6-carboxylateA solution of ethyl 2-mercaptoacetate (1.473 mL) in DMF (48 mL) was ice-cooled and treated with sodium hydride (540 mg of a 60% dispersion in oil). After 1 hour methyl 6-amino-5-bromopyridine-2-carboxylate (3 g) (T. R. Kelly and F. Lang, J. Org. Chem. 61, 1996, 4623-4633) was added and the mixture stirred for 16 hours at room temperature. The solution was diluted with EtOAc (1 litre), washed with water (3×300 mL), dried and evaporated to about 10 mL. The white solid was filtered off and washed with a little EtOAc to give the ester (0.95 g); MS (APCl-) m/z223 ([M-H]-, 100%).

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, 178876-82-9, Methyl 6-amino-5-bromopicolinate.

Reference:
Patent; Glaxo Group Limited; US2008/194547; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem