Category: pyridine-derivatives

Application of 1268521-33-0, 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 1268521-33-0, name is 3-Bromo-2-chloro-5-nitropyridin-4-amine. This compound has unique chemical properties. The synthetic route is as follows.

A dried RBF was charged with Na2CO3 (61.7 g, 582 mmol), in water (75 mL) and was stirred until a solution was obtained. THF (750 mL) and EtOH (150 mL) were then added and the solution was sparged with argon during the following additions; 3-bromo-2-chloro-5-nitropyridin-4-amine (49 g, 194 mmol) was charged, and phenylboronic acid (53.5 g, 388 mmol). After 20 min of sparging argon, Pd(PPh3)4 (17.9 g, 15.5 mmol) was charged. The reaction was sealed and was run under argon at 85 C. Once the reaction was deemed complete it was concentrated directly. To the residual was added water, and the mixture extracted with EtOAc. The combined organic fractions were combined, dried with MgSO4 and concentrated. The residual was purified via silica gel column chromatography, eluting with 0-30% EtOAc/Hexane. 2-(4-amino-3-bromo-5-nitropyridin-2-yl)phenol was isolated as a red semi solid (39 g, 65% yield).

According to the analysis of related databases, 1268521-33-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Universal Display Corporation; Layek, Suman; Ji, Zhiqiang; Dyatkin, Alexey Borisovich; Boudreault, Pierre-Luc T.; Tsai, Jui-Yi; (251 pag.)US2019/393431; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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.174669-74-0, name is 2-Fluoropyridin-3-ol, molecular formula is C5H4FNO, molecular weight is 113.09, as common compound, the synthetic route is as follows.COA of Formula: C5H4FNO

General procedure: Using an apparatus previously described for method B [21] , potassium hydroxide (2.52 g, 45 mmol, 15 equiv) and water (2.52 g) were added to the reaction vessel and the mixture was allowed to stir until the potassium hydroxide was almost completely dissolved. Then, 2-bromo-3-pyridinol (0.354 g, 3 mmol) was added and the mixture stirred for 30 min, after which acetonitrile (10 mL) was added via syringe and the mixture stirred at room temperature. Fluoroform was then bubbled slowly into the mixture for 2 h, after which the resulting mixture was stirred for one additional hour. After being quenched with water and extracted with ethyl acetate, the ethyl acetate layer was washed with a saturated solution on sodium hydroxide, separated and concentrated. Additional impurities were removed via column chromatography on silica gel using an 80:20 mixture of hexanes/methylene chloride to give a 53% yield of the liquid product, 2-bromo-3-difluoromethoxypyridine (3d):

At the same time, in my other blogs, there are other synthetic methods of this type of compound,174669-74-0, 2-Fluoropyridin-3-ol, and friends who are interested can also refer to it.

Reference:
Article; Thomoson, Charles S.; Wang, Linhua; Dolbier, William R.; Journal of Fluorine Chemistry; vol. 168; (2014); p. 34 – 39;,
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. 1990-90-5, name is 3-Methylpyridin-4-amine. A new synthetic method of this compound is introduced below., Safety of 3-Methylpyridin-4-amine

To a solution of intermediate 2c (100 mg) in CH2Cl2(7 mL) were consecutively added N,N-Diisopropylethylamine (140 muL), 3-methylpyridin-4-amine (40 mg) and bromotripyrrolidinophosphonium hexafluorophosphate (230 mg) and the mixture was stirred at ambient temperature for 2 h. The volatiles were removed under reduced pressure and the residue was purified by column chromatography (Interchim cartridge50SiHP/25 g, Cy/EtOAc) to yield the desired compound (84% yield). [0430] LC-MS (Method 2): m/z [M+H]+=353.2 (MW calc.=352.39); Rt=0.48 min

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, 1990-90-5, 3-Methylpyridin-4-amine.

Reference:
Patent; Gruenenthal GmbH; Nordhoff, Sonja; Wachten, Sebastian; Kless, Achim; Voss, Felix; Ritter, Stefanie; US2014/194452; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 694-85-9, Adding some certain compound to certain chemical reactions, such as: 694-85-9, name is 1-Methylpyridin-2(1H)-one,molecular formula is C6H7NO, 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 694-85-9.

At 0 ¡ã C, 1 mmol of N-methyl-2-pyridone was added to the reactor,1.2 mmol of compound of formula (II-1), 0.1 mmolDi (1,5-cyclooctadiene) rhodium tetrafluoroborate,0.1 mmol of ligand L, 8 ml of N, N-dimethylformamide and 2 ml of toluene,The reaction was stirred at 60 ¡ã C for 6 hours. After the reaction was completed, the reaction mixture was poured into water,And extracted with ethyl acetate, the organic phase was combined to remove the solvent,The resulting residue was subjected to silica gel column chromatography to give a compound of formula (III-1) in a yield of 89.5percent.

According to the analysis of related databases, 694-85-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Zhou Xiaofang; (5 pag.)CN106905230; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 26218-75-7, name is Methyl 6-bromopicolinate. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of Methyl 6-bromopicolinate

Methylmagnesium iodide (3M in Et20, 1.50 ml, 4.48 mmol) was added to a solution of methyl 6-bromopyridine-2- carboxylate (0.430 g, 1.99 mmol) in dry Et20 (1 5 ml) under N2. After 5 min at RT the reaction was quenched with 1 M HCI (10 ml) and extracted with EtOAc (15 ml). The organic extract was washed with sat. NaHC03 solution (1 5 ml) and brine (10 ml), dried (MgS04) and concentrated in vacuo. The desired product was obtained as a yellow oil (0.365 g, 1.69 mmol, 85%). Rf 0.60 (1 :1 Hexane:EtOAc); I R (cm-1 ) 3420, 2975, 2930, 1731 , 1701 , 1 580, 1 553; 1 H NMR (400 MHz, DMSO-d6) 1.42 (6H, s, C(CH2)2), 5.33 (1 H, s, OH), 7.47 (1 H, dd, J = 7.7, 0.9 Hz, H-5), 7.67 (1 H, dd, J = 7.7, 0.9 Hz, H-3), 7.73 (1 H, dd, J = 7.7, 7.7 Hz, H-4); 13C N MR (125 MHz, DMSO-d6) 30.9 (C(CH2)2), 72.6 (C(CH2)2), 1 18.5 (Ar-C), 126.0 (Ar-C), 140.4 (Ar-C), 140.5 (Ar-C), 170.8 (Ar-C).

With the rapid development of chemical substances, we look forward to future research findings about 26218-75-7.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF COLORADO, A BODY CORPORATE; REIGAN, Philip; MATHESON, Christopher; (71 pag.)WO2017/75629; (2017); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1480-65-5, 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 1480-65-5, name is 5-Chloro-2-fluoropyridine. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 5-bromo-2-(tert-butylthio)aniline (300 mg, 1 .2 mmol), 5-chloro-2-fluoropyridine (157 mg, 1 .2 mmol), Cs2C03 (782 mg, 2.4 mmol) in NMP (5 mL) was purged with N2 before heated to 140 ¡ãC for 8 h. The reaction mixture was then cooled down to room temperature. Water was added and the mixture was partitioned between EtOAc (50 mL) and water (15 mL). The layers were separated and the organic layer was washed with brine (20 mL), dried with Na2S04, and concentrated. The crude product was purified by flash chromatography (silica gel, 5-20percent EtOAc in petroleum ether) to give the title compound (100 mg, 24percent) as a yellow solid. LCMS (M+H)+: m/z = 371 .43.

According to the analysis of related databases, 1480-65-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; JOHNS, Brian Alvin; KAZMIERSKI, Wieslaw Mieczyslaw; DE LA ROSA, Martha Alicia; SAMANO, Vicente; (84 pag.)WO2017/195149; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 875781-15-0, Adding some certain compound to certain chemical reactions, such as: 875781-15-0, name is 5-Bromo-2-fluoronicotinaldehyde,molecular formula is C6H3BrFNO, 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 875781-15-0.

To a stirred solution of 5-bromo-2-fluoronicotinaldehyde (XV) (250 g, 1.23 mol, 1.0 eq) in EtOH (2.50 L) was added hydrazine hydrate (221 g, 4.41 mol, 3.6 eq) at 25C. The reaction was then heated to 75~80C and stirred for 12 h. The solvent was removed under reduced pressure at 45C. The residual crude solid was triturated in water (750 mL) and EtOH (250 mL). The resultant suspension was filtered and washed with ethanol to give 5 -bromo- lH-pyrazolo[3,4- b]pyridine (XVI) (135 g, 0.68 mol, 55.4% yield) as yellowish solid which was used directly for the next step without further purification. ESIMS found for CeLLtBrNs mlz 199.1 (M+H).

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. 875781-15-0, 5-Bromo-2-fluoronicotinaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SAMUMED, LLC.; KC, Sunil Kumar; WALLACE, David Mark; CAO, Jianguo; CHIRUTA, Chandramouli; HOOD, John; (252 pag.)WO2017/23987; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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.929000-66-8, name is 3-Bromo-6-chloropyridine-2-carboxylic acid, molecular formula is C6H3BrClNO2, molecular weight is 236.4505, as common compound, the synthetic route is as follows.Recommanded Product: 3-Bromo-6-chloropyridine-2-carboxylic acid

To a stirred suspension of 3-bromo-6-chloropyridine-2-carboxylic acid (3.6 g, 15. mmol) in 1 ,4-dioxane (35 mL) was added (1 R,2R)-N,N-dimethylcyclohexane-1 ,2- diamine (220 mg, 1 .5 mol), Cs2C03 (10 g, 31 mmol), 1 H-1 ,2,3-triazole (2.1 g, 31 mmol), water (0.3 mL) and the mixture was degassed under nitrogen for 10 mins. Cul (295 mg, 1.6 mmol) was added and the mixture was heated at 100C for 6 hrs. The reaction mixture was then allowed to cool to ambient temperature, and concentrated in vacuo. MeOH (20 mL) was added to the residue and the mixture was acidified to pH 2 with 6N hydrochloric acid (approx 6 mL) and concentrated in vacuo. MeOH (20 mL) was added to the residue and concentrated in vacuo (x2). The residue was dissolved in MeOH (15 mL) and DCM (35 mL) and cooled to 0C. TMS diazomethane (39 mL, 77 mmol) was added dropwise (over 15 mins) and the reaction mixture was stirred at ambient temperature for 18 hrs. The reaction mixture was concentrated in vacuo. The crude product was purified by chromatography on the Biotage Isolera Four (100 g column, 10 to 80% EtOAc in heptane) to afford the title compound as an oil (1 .8 g). LCMS (Method G): 1 .03 min, 239 [M+H]+

At the same time, in my other blogs, there are other synthetic methods of this type of compound,929000-66-8, 3-Bromo-6-chloropyridine-2-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; C4X DISCOVERY LIMITED; BLANEY, Emma Louise; MARTIN, Barrie Phillip; NOWAK, Thorsten; WATSON, Martin John; (212 pag.)WO2016/34882; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1072-97-5, 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. 1072-97-5, name is 5-Bromopyridin-2-amine. A new synthetic method of this compound is introduced below.

(a) A mixture of concentrated sulphuric acid (35 ml) and nitric acid (35 ml) was added dropwise with stirring to a chilled (5 C.) solution of 2-amino-5-bromopyridine (50.3 g) in concentrated sulphuric acid (240 ml) maintaining the temperature of the reaction mixture at 5-6 C. throughout the addition. When the addition was complete, the reaction mixture was stirred for a further 1.0 hr. at 5-8 C. and then warmed to 30 C. and allowed to stand for ca 18 hr. Further concentrated nitric acid (35 ml) was added portionwise to the reaction mixture with stirring while maintaining the temperature at 30-40 C. A portion (50 ml) of the solution was poured into hot (ca 70 C.) water (100 ml) with rapid stirring and this mixture was heated to 120 C. Gas evolved. When the evolution of gas ceased further portions (75 ml) of the reaction mixture were added maintaining the temperature at 120 C. When the additions were completed, the solution obtained was poured into ice (1 kg) and chilled in a salt/ice bath. Fine orange crystals formed which were removed by filtration and recrystallized from dimethylformamide/water to give 2-hydroxy-3-nitro-5-bromopyridine (23.5 g) m.p. 240-243 C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1072-97-5, 5-Bromopyridin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; Smith Kline & French Laboratories Limited; US4532252; (1985); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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.72537-17-8, name is 3-Chloro-2-fluoro-5-(trifluoromethyl)pyridine, molecular formula is C6H2ClF4N, molecular weight is 199.53, as common compound, the synthetic route is as follows.Quality Control of 3-Chloro-2-fluoro-5-(trifluoromethyl)pyridine

500mL glass bottle,48.6 g (0.243 mol) of 2-fluoro-3-chloro-5-trifluoromethylpyridine,Dichlorohexane 200g,40.4 g (0.247 mol) of 30% sodium cyanide,4 g (0.018 mol) of benzyltriethylammonium chloride,Warmed to 20 C,Timed reaction 10h,After the water treatment,After the oil phase is recovered from dichloroethane,100-110 C / 15 mmHg fractions were collected.46.7 g of a colorless liquid 2-cyano-3-chloro-5-trifluoromethylpyridine was obtained.The content of 2-cyano-3-chloro-5-trifluoromethylpyridine in the product was 99.6% (GC)The total yield of the two-step reaction is 90.1%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,72537-17-8, 3-Chloro-2-fluoro-5-(trifluoromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; Inner Mongolia Jiaruimi Fine Chemical Co., Ltd.; Dong Yongxia; Xiang Bin; Li Jun; (5 pag.)CN107286087; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem