Category: 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. 917023-06-4, name is Methyl 2-(5-bromopyridin-2-yl)acetate. This compound has unique chemical properties. The synthetic route is as follows. name: Methyl 2-(5-bromopyridin-2-yl)acetate

To a solution of methyl 2-(5-bromopyridin-2-yl)acetate (5.50 g, 23.91 mmol) and 1,4- dioxaspiro[4.5]decan-8-ylmethyl trifluoromethanesulfonate (6.85 g, 19.13 mmol) in THF (100 mL) was added LiHMDS (27.50 mL, 27.50 mmol, 1 M in THF) at -78C. The reaction mixture was stirred at 15C for 16 h under a nitrogen atmosphere. LC-MS showed the reaction was complete. The mixture was quenched with saturated NH4Cl solution (30 mL), diluted with water (60 mL), and extracted with EtOAc (50 mL x 3). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by chromatography (SiO2, 0-20% EtOAc/PE) to give the title compound.1H NMR (CDCl3, 400 MHz^^^^^^^^^^G^^J=2.0 Hz, 1H), 7.76 (dd, J=8.4, 2.2 Hz, 1H), 7.20 (d, J=8.6 Hz, 1H), 3.85-3.94 (m, 5H), 3.66 (s, 3H), 2.00-2.05 (m, 1H), 1.79-1.87 (m, 1H), 1.61-1.75 (m, 4H), 1.37-1.47 (m, 2H), 1.17-1.29 (m, 3H). MS (ESI) m/z 384.1/386.1 (M+H).

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, 917023-06-4, Methyl 2-(5-bromopyridin-2-yl)acetate.

Reference:
Patent; MERCK SHARP & DOHME CORP.; SHEN, Dong-Ming; KUANG, Rongze; KUMAR, Puneet; DUFFY, Joseph, L.; ZHU, Cheng; ALI, Amjad; YANG, Meng; DEBENHAM, John, S.; (124 pag.)WO2018/39094; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 3510-66-5 ,Some common heterocyclic compound, 3510-66-5, molecular formula is C6H6BrN, 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 compound C1 (78.0 g, 456 mmol) and CuCN (45.2 g, 502 mmol) in 400 nriL of DMF was refluxed for 3 h. The mixture was concentrated under vacuum and the residue purified by chromatography on silica gel (eluent: PE/EtOAc = 10/1) to give 7.7 g of compound C2 as a white solid (Yield: 14.3percent).

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. 3510-66-5, 2-Bromo-5-methylpyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PHENEX PHARMACEUTICALS AG; KREMOSER, Claus; ABEL, Ulrich; STEENECK, Christoph; KINZEL, Olaf; WO2011/20615; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 17282-00-7, 3-Bromo-5-methylpyridin-2-amine, 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, Quality Control of 3-Bromo-5-methylpyridin-2-amine, blongs to pyridine-derivatives compound. Quality Control of 3-Bromo-5-methylpyridin-2-amine

General procedure: Under N2 atmosphere, to a solution of palladium acetate (120 mg, 0.53 mmol, 5 mol %) and XANTPHOS (309 mg, 0.53 mmol, 5 mol %) in anisole (30 mL) was added 3-bromo-5-methyl-pyridin-2-ylamine (5) (2.0 g, 10.7 mmol, 1.0 equiv), aryl iodides (6) (10.7 mmol) and cesium carbonate (4.9 g, 15.0 mmol, 1.4 equiv), and the mixture was stirred at 130 C for 1-13 h. After cooling to room temperature, water (40 mL) was added to the mixture. The mixture was concentrated in vacuo and ethyl acetate (100 mL) was added to the residue. The organic layer was washed with water (20 mL) and concentrated in vacuo to give the crude product, which was purified by flash chromatography to give 7.

The synthetic route of 17282-00-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mineno, Masahiro; Sera, Misayo; Ueda, Tsuyoshi; Mizuno, Masahiro; Yamano, Mitsuhisa; Mizufune, Hideya; Zanka, Atsuhiko; Tetrahedron; vol. 70; 35; (2014); p. 5550 – 5557;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 30529-70-5, 2-Chloro-6-methylnicotinic acid, 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, COA of Formula: C7H6ClNO2, blongs to pyridine-derivatives compound. COA of Formula: C7H6ClNO2

Description 47: methyl l-chloro–methyl-S-pyridinecarboxylate (D47); To a solution of 2-chloro-6-methyl-3-pyridinecarboxylic acid (8 g, 46.6 mmol) (available from Sigma-Aldrich No.357847) in DCM (100 ml) and MeOH (50.0 ml) stirred under nitrogen at room temperature was added TMS-diazomethane 2 M in hexane (46.6 ml, 93 mmol). The reaction mixture was stirred at room temperature for 20 minutes. The solvents were removed to give the title compound D47 (7 g).MS: (ES/+) m/z: 186 (M+l) C8H8ClNO2 requires 185.1H NMR (400 MHz, CDCl3) ppm 8.10 (d, 1 H), 7.18 (d, 1 H), 3.96 (s, 3 H), 2.61 (s, 3 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,30529-70-5, 2-Chloro-6-methylnicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; GLAXO GROUP LIMITED; AMANTINI, David; DI FABIO, Romano; WO2010/122151; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 100-26-5 ,Some common heterocyclic compound, 100-26-5, molecular formula is C7H5NO4, 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.

PREPARATION 1 dimethyl Pyridine-2,5-dicarboxylate To a stirred slurry of 2,5-pyridinedicarboxylic acid (2407 g; 14.4 mol) in methanol (8.0 liter) at -5 to -10C, thionylchloride (3430 g; 2.10 liters; 28.8 mol) was added dropwise while maintaining the temperature in the -5 to -10C range. After completing the addition, the reaction was allowed to warm to ambient temperature, and stirred for 18 hours. The resulting solution was concentrated in vacuo to a volume of 4 liters, and an equal volume of water was added. The PH of the well-stirred mixture was then adjusted to 10 with saturated aqueous sodium carbonate. Solids were removed by filtration. The organic layer of the filtrate was separated, washed with water (8 liters), and dried in vacuo to afford the title compound (2250 g; 80% yield) as an amorphous solid.

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. 100-26-5, 2,5-Pyridinedicarboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PFIZER INC.; EP536173; (1995); B1;,
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.6602-32-0, name is 2-Bromo-3-hydroxypyridine, molecular formula is C5H4BrNO, molecular weight is 174, as common compound, the synthetic route is as follows.HPLC of Formula: C5H4BrNO

Preparation 1022-Bromo- -difluoromethoxypyridineTo a solution of 2-bromo-3-pyridinol (1 .26 g, 7.23 mmol) in DMF (35 mL) and water (5 mL) was added sodium chlorodifluoroacetate (2.93 g, 18.1 mmol) followed by cesium carbonate (4.71 g, 14.5 mmol). The reaction was heated to 100 C for 36 hours before partitioning between EtOAc and water. The organic layer was collected, dried over magnesium sulfate and concentrated in vacuo. The residue was purified using silica gel column chromatography eluting with EtOAc:heptane 1 :3 to afford the title compound as a colourless oil (570 mg, 35%).1H NMR (400 MHz; DMSO-d6): delta 7.15-7.55 (t, 1 H), 7.55 (m, 1 H), 7.80 (m, 1 H), 8.25 (m, 1 H).LCMS Rt = 1 .91 minutes MS m/z 226 [M79BrH]+

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6602-32-0, 2-Bromo-3-hydroxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; PFIZER LIMITED; BROWN, Alan Daniel; RAWSON, David James; STORER, Robert Ian; SWAIN, Nigel Alan; WO2012/7869; (2012); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 128072-93-5, 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. 128072-93-5, name is Ethyl 5-chloropicolinate, molecular formula is C8H8ClNO2, 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.

Intermediate A-28A: tert-Butyl (2-(5-chloropicolinoyl)-6-methoxyphenyl)carbamate [0351] tert-butyl 2-methoxyphenylcarbamate (548 mg, 2.454 mmol) in ether (6 mL) under N2 was added t-BuLi (3.2 mL, 5.44 mmol). After stirring for 2.5 h, the reaction mixture was cooled to -78 C. To the reaction mixture was added a solution of ethyl 5-chloropicolinate (564.5 mg, 3.04 mmol) in ether (12 mL) dropwise via cannula over 5 min. The reaction mixture was stirred for 60 min, and then warmed to room temperature. After 1.5 h, to the reaction mixture was added H2O with vigorous stirring. The reaction mixture was diluted with EtOAc, and the organic phase was separated, washed with sat NaCl then dried (Na2SO4), filtered and concentrated to yield the product Intermediate A-29A (511.5 mg, 57.4% yield)) as a yellow solid: 1H NMR (400 MHz, chloroform-d) delta ppm 8.55 (1H, dd, J=2.3, 0.6 Hz), 8.08 (1H, dd, J=8.4, 0.7 Hz), 7.80 (1H, dd, J=8.4, 2.4Hz), 7.16-7.25 (2H, m), 7.06 (1H, dd, J=7.5, 2.2Hz), 6.90 (1H, s), 3.92 (3H, s), 1.28 (9H, s).

According to the analysis of related databases, 128072-93-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Gavai, Ashvinikumar V.; DeLucca, George V.; O’Malley, Daniel; Gill, Patrice; Quesnelle, Claude A.; Fink, Brian E.; Zhao, Yufen; Lee, Francis Y.; US2014/87992; (2014); 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. 885276-93-7, name is Ethyl 5-bromopyrazolo[1,5-a]pyridine-3-carboxylate, the common compound, a new synthetic route is introduced below. Safety of Ethyl 5-bromopyrazolo[1,5-a]pyridine-3-carboxylate

A solution of ethyl 5-bromopyrazolo[1,5-a]pyridine-3-carboxylate (240 mg, 0.89 mmol) in 40% H2SO4 (12 mL) was stirred at 100 C. for 4 hours, then cooled to rt, and neutralized to pH=7 with aq. NaOH (6 M) in ice bath. The resulted mixture was extracted with DCM (25 mL×2). The combined organic phases were dried over anhydrous Na2SO4 and concentrated in vacuo to give the title compound as a light yellow solid (175 mg, 99.5%). MS (ESI, pos. ion) m/z: 196.9 [M+H]+.

The synthetic route of 885276-93-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; CALITOR SCIENCES, LLC; Xi, Ning; US2014/234254; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 889865-45-6, 2,3-Dichloro-4-iodopyridine, 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: C5H2Cl2IN, blongs to pyridine-derivatives compound. Formula: C5H2Cl2IN

A solution of 3-amino-5-chloropyrazine-2-thiol (TFA salt: 0.50 g, 1.814 mmol) in dioxane (90 mL) was degassed with nitrogen for 10 min. Then, 2,3-dichloro-4-iodopyridine (0.0.99 g, 3.63 mmol), Xantphos (0.105 g, 0.181 mmol), Pd2(dba)3 (0.083 g, 0.091 mmol), and DIPEA (0.95 mL, 5.44 mmol) were added. The resulting mixture was stirred at 105 C for 10 h, filtered through Celite and concentrated. The crude was purified by silica chromatography (0- 10% gradient of EtOAc DCM). NMR (400 MHz, DMSO-t/6) delta ppm 8.13 (d, J=5.3 Hz, 1 H), 7.95 (s, 1 H), 7.30 (br. s, 2 H), 6.83 (d, J=5.3 Hz, 1 H). MS m/z 306.9 (M+H)+

The synthetic route of 889865-45-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; CHEN, Christine Hiu-tung; CHEN, Zhuoliang; DORE, Michael; FORTANET, Jorge Garcia; KARKI, Rajesh; KATO, Mitsunori; LAMARCHE, Matthew J.; PEREZ, Lawrence Blas; SMITH, Troy Douglas; WILLIAMS, Sarah; GIRALDES, John William; TOURE, Bakary-barry; SENDZIK, Martin; WO2015/107495; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 66572-56-3 ,Some common heterocyclic compound, 66572-56-3, molecular formula is C6H4BrNO2, 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.

Stepl : 2-phenylisonicotinic acid 2-bromoisonicotinic acid (0.210 g, 1 .040 mmol) was dissolved in degassed DME (Volume: 8 ml) under nitrogen. Tetrakis(triphenylphosphine)palladium(0) (0.060 g, 0.052 mmol) was added, the resulting reaction mixture was stirred for 15min.Then aqueous potassium carbonate (4.16 ml, 8.32 mmol) and phenylboronic acid (0.171 g, 1 .403 mmol) were added subsequently. The resulting RM was refluxed at 95 C for 18h and then cooled to rt. After filtration over celite the reaction mixture was acidified to pH 3-4 and the white precipitate was filtered off and washed with water. This resulted in a white powder after recrystallization from 2-methoxyethanol. Yield: 0.1 06 g, 57%. 1 H NMR (400 MHz, DMSO-c): delta 7.44 – 7.60 (m, 3H), 7.71 – 7.86 (dd, J = 4.9, 1 .5 Hz, 1 H), 8.05 – 8.19 (m, 2H), 8.23 – 8.35 (t, J = 1 .2 Hz, 1 H), 8.79 – 8.93 (dd, J = 5.1 , 0.8 Hz, 1 H), 13.56 – 13.97 (s, 1 H). UPLC I (ESI) Rt 1 .37 min, m/z 200.5 [M+H]+ (92%). – –

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. 66572-56-3, 2-Bromoisonicotinic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UNIVERSITEIT ANTWERPEN; FOX CHASE CANCER CENTER; JANSEN, Koen; DE MEESTER, Ingrid; HEIRBAUT, Leen; CHENG, Jonathan D; JOOSSENS, Jurgen; AUGUSTYNS, Koen; VAN DER VEKEN, Pieter; WO2013/107820; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem