Tag: M.W:200-300

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. 1086381-43-2, name is 2-Bromo-4-isopropylpyridine. A new synthetic method of this compound is introduced below., SDS of cas: 1086381-43-2

To a heat dried flask, phenylboronic acid (319.9 mg, 1.05 equiv., 2.624 mmol), potassium carbonate (1.036 g, 3 equiv., 7.5 mmol) and palladium(ii) acetate (56 mg, 0.1 equiv., 0.24990mmol%) were added. The flask was sealed and vacuumed and backfilled with nitrogen 3 times. Degassed ethanol (11.3 mL, 0.22 1 M) and water (2.8 mL, 0.885 M) were added, followed by 2-bromo-4-isopropyl-pyridine (500 mg, 2.4990 mmol), and the reaction was heated to 80C. The reaction was ran overnight, then was cooled to room temperature, was filtered through silica gel(isopropyl acetate eluting). The crude reaction was concentrated and purified by column chromatography to give a pale yellow oil (118.4 mg, 24% yield). 1H NMR (400 MHz, Chloroform-d) delta 8.58 (d, J = 5.2 Hz, 1H), 8.02 – 7.90 (m, 2H), 7.59- 7.54 (m, 1H), 7.50-7.34 (m, 4H), 7.08 (dd, J = 5.2, 1.6 Hz, 1H), 2.94 (hept, J = 6.9 Hz, 1H), 1.29 (d, J = 7.0 Hz, 6H).

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, 1086381-43-2, 2-Bromo-4-isopropylpyridine.

Reference:
Patent; GENENTECH, INC.; XENON PHARMACEUTICALS INC.; BERGERON, Phillipe; BURFORD, Kristen; CHOWDHURY, Sultan; DEHNHARDT, Christoph Martin; FOCKEN, Thilo; GRIMWOOD, Michael Edward; HASAN, Abid; LAI, Kwong Wah; LIU, Zhiguo; MCKERRALL, Steven; NGUYEN, Teresa Phuongtram; SAFINA, Brian; SUTHERLIN, Daniel; TAN, Wang Tao; (470 pag.)WO2017/58821; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1206978-11-1, Adding some certain compound to certain chemical reactions, such as: 1206978-11-1, name is 2-Bromo-3-(trifluoromethoxy)pyridine,molecular formula is C6H3BrF3NO, 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 1206978-11-1.

To a stirred mixture of 2-bromo-3- (trifluoromethoxy) pyridine (300 mg, 1.24 nMol, 1 equiv) and Zn (CN) 2 (291.2 mg, 2.48 nMol, 2 equiv) in THF (15 mL) and H 2O (3 mL) , t-BuXantPhos-Pd-G3 (197.0 mg, 0.25 nMol, 0.2 equiv) and t-BuXantPhos (171.3 mg, 0.25 nMol, 0.2 equiv) under nitrogen atmosphere at RT. The resulted mixture was stirred for 2h at 80 under nitrogen atmosphere. The solvent was removed under reduced pressure. The residue was purified by Prep-TLC (CH 2Cl 2 /MeOH 20: 1) to afford 3- (trifluoromethoxy) pyridine-2-carbonitrile (200 mg, 85.76%) as a white solid. LCMS: m/z (ESI) , [M+H] + = 188.9.

According to the analysis of related databases, 1206978-11-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DIZAL (JIANGSU) PHARMACEUTICAL CO., LTD.; QI, Changhe; TSUI, Honchung; ZENG, Qingbei; YANG, Zhenfan; ZHANG, Xiaolin; (399 pag.)WO2020/35052; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 132521-70-1 , The common heterocyclic compound, 132521-70-1, name is 6-(4-Methylpiperazin-1-yl)nicotinic acid, molecular formula is C11H15N3O2, 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 mixture of 6-(4-methylpiperazin- 1 -yl)nicotinicacid (150 mg, crude), tert-butyl 3-aminobiphenyl-4-ylcar-bamate (173 mg, 0.6 mmol) and EDCI (260 mg, 1.35 mmol)in pyridine (10 mE) was stirred at room temperature for overnight. The mixture was poured into water (20 mE), filtered to afford desired compound (300 mg, 89%) as a yellow solid.

The synthetic route of 132521-70-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Regenacy Pharmaceuticals, LLC; van Duzer, John H.; Mazitschek, Ralph; (123 pag.)US2018/141923; (2018); 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. 41668-13-7, name is 5-Bromo-6-hydroxynicotinic acid, molecular formula is C6H4BrNO3, 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 5-Bromo-6-hydroxynicotinic acid

[0543] A solution of Example 117a (1 g, 4.58 mmol) and K2C03 (1.56 g, 13.76 mmol) in 10 mL of DMF, and was added Mel (0.7 mL, 11.46 mmol), the reaction was stirred at rt for 2.5 h. LCMS (BD01075-068) showed SM consumed, the mixture was poured into 30 mL water and stirred for 10 min. The mixture was extracted with EA (10 mL * 3). The combined organic phase was dried over MgS04, filtrated and the filtrate was concentrated under reduced pressure to get desired product (0.82 g, yield 73%) as yellow solid. LCMS [M+l] + = 246.0

With the rapid development of chemical substances, we look forward to future research findings about 41668-13-7.

Reference:
Patent; FRONTHERA U.S. PHARMACEUTICALS LLC; JIN, Bohan; DONG, Qing; HUNG, Gene; (227 pag.)WO2018/151830; (2018); 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. 17117-17-8, name is 3-Bromo-5-ethoxypyridine. This compound has unique chemical properties. The synthetic route is as follows. Safety of 3-Bromo-5-ethoxypyridine

Under a nitrogen atmosphere, a mixture of 5-ethoxy-3-bromopyridine (1.20 g, 5.94 mmol), N-methyl-N-(tert-butoxycarbonyl)-4-penten-2-amine (1.18 g, 5.94 mmol), palladium(II) acetate (13.5 mg, 0.06 mmol), tri-o-tolylphosphine (73.1 mg, 0.24 mmol), triethylamine (1.5 mL, 10.8 mmol), and anhydrous acetonitrile (3 mL) was stirred and heated under reflux at 80-85 C. for 28 h. The resulting mixture, containing beige solids, was cooled to ambient temperature, diluted with water (20 mL), and extracted with CHCl3 (3*20 mL). The combined light-yellow CHCl3 extracts were dried (Na2SO4), filtered, concentrated by rotary evaporation, and vacuum dried producing a yellow oil (1.69 g). The crude product was purified by column chromatography on silica gel (100 g), eluding with ethyl acetate-hexane (1:1, v/v). Selected fractions containing the product (Rf 0.20) were combined, concentrated by rotary evaporation, and the residue was vacuum dried to give 0.67 g (35.2%) of a light-yellow oil. (4E)-N-Methyl-5-(5-ethoxy-3-pyridyl)-4-penten-2-amine

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, 17117-17-8, 3-Bromo-5-ethoxypyridine.

Reference:
Patent; Targacept, Inc.; US6979695; (2005); B2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 89364-04-5, 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 89364-04-5 as follows.

2.02 g (10.0 mmol) of 3-bromo-4-nitropyridine,2.20 g (11.0 mmol) of 4-bromophenylboronic acid,0.46 g (0.4 mmol) of tetraphenylphenylphosphine palladium,1.33 g (25 mmol) of Na2CO3 was dissolved in 60 mL of dioxane and 10 mL of water,110 reflux 12h, cooling,Poured into 80mL water,After extraction with 100 mL of ethyl acetate three times,Dried over anhydrous magnesium sulfate.The solvent was removed in vacuo,The solid was subjected to column chromatography,To give 2.1 g of product as a yellow solid (yield: 75%)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,89364-04-5, its application will become more common.

Reference:
Patent; Zhejiang University; He, Qinggang; Ren, Rong; Zhang, Kai; Zhang, Hong; Tian, Mei; (9 pag.)CN106588915; (2017); A;,
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. 103058-87-3, name is 5-Bromo-2-methoxynicotinaldehyde, the common compound, a new synthetic route is introduced below. Recommanded Product: 103058-87-3

a) 5-Bromo-2-methoxv-3- (4-methoxv-but-1 (E, Z)-envl)-pvridine; 2. 45 ml of a 1M solution of sodium-bis(trimethylsilyl) amide in tetrahydrofuran are added. to a suspension of 2. 4 mmol (3-methoxy-propyl)-triphenyl-phosphonium bromide [111088-69-8] in 8 mi tetrahydrofuran unter an argon atmosphere at 0C. The reaction mixture is stirred for 30 minutes at 0C and then 1. 6 mmol 5-bromo-2-methoxy-pyridine-3-carbaldehyde [103058-87- 3] are added. The reaction mixture is warmed to room temperature and then diluted with tert- butyl methyl ether. The solution is washed with saturated aqueous sodium hydrogencarbonate solution. The organic layer is dried over sodium sulphate, filtered and concentrated. The title compound is obtained from the residue by means of flash chromatography (SiO2 60F) and identified based on its Rf value

The synthetic route of 103058-87-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SPEEDEL EXPERIMENTA AG; WO2005/90304; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 204378-41-6, 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 204378-41-6, name is Methyl 6-chloro-4-methoxypicolinate. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of methyl 6-chloro-4-methoxypicolinate 25 (600 mg, 2.98 mmol) and cyclopentylzinc bromide (12 mL of a 0.5 M solution in THF) in dioxane (10 mL) Pd(dppf)Cl2 (25 mg, 30 mol) was added. The mixture was stirred at 75°C for 18 h. The mixture was cooled the rt and the reaction was quenched by carefully adding water (20 mL). The mixture was filtered and the filtrate was extracted with EA (2×100 mL). The combined organic extracts were dried over MgSO4, filtered and concentrated. The crude product was purified by CC on silica gel eluting with heptane:EA 4:1 to give methyl 6-cyclopentyl-4-methoxypicolinate 30 (580 mg, ~80percent) as a pale yellow oil containing approx. 30percent of cyclopentyl 6-cyclopentyl-4-methoxypicolinate

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 204378-41-6, Methyl 6-chloro-4-methoxypicolinate.

Reference:
Article; Bolli, Martin H.; Lescop, Cyrille; Birker, Magdalena; De Kanter, Ruben; Hess, Patrick; Kohl, Christopher; Nayler, Oliver; Rey, Markus; Sieber, Patrick; Velker, Joerg; Weller, Thomas; Steiner, Beat; European Journal of Medicinal Chemistry; vol. 115; (2016); p. 326 – 341;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 727356-19-6, 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 727356-19-6 as follows.

Potassium pthalimide (1.23 kg, 6.0 mol), potassium carbonate (2.07 kg, 15 mol) were dissolved in DMF (12.5L). A214.1a was added slowly and the reaction stirred at room temperature overnight. TLC analysis indicated disappearance of starting material. The product was filtered to yield A214.1 (2.5kg wet weight- used in next step without further drying).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,727356-19-6, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2006/122137; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 887707-23-5, 2-Hydroxy-5-iodo-3-(trifluoromethyl)pyridine, 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, Formula: C6H3F3INO, blongs to pyridine-derivatives compound. Formula: C6H3F3INO

To a solution of 5-iodo-3-(trifluoromethyl)pyridin-2-ol (4.0 g, 13.8 mmol) in DMF (50 mL), CuCN (2.48 g, 27.7 mmol) was added. The mixture was degassed with 3 vacuum-nitrogen cycles and stirred at 120 C for 16 h. The reaction was cooled to room temperature, poured into water (60 mL), diluted with 3 M HC1 (30 mL) then extracted with EtOAc (3 x 80 mL). The combined organic layers were washed with brine (2 c 60 mL), dried over Na2S04, filtered, and concentrated to give 6-hydroxy-5-(trifluoromethyl)nicotinonitrile (2.5 g, crude) as an oil. 1H NMR (400 MHz, CDCI3): d 8.03 (s, 2H); MS: 189.0 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,887707-23-5, 2-Hydroxy-5-iodo-3-(trifluoromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; METACRINE, INC.; SMITH, Nicholas D.; HUDSON, Andrew R.; CHEN, Mi; NAGASAWA, Johnny Y.; (265 pag.)WO2019/241751; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem