Tag: M.W:200-300

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

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

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. 13534-89-9, name is 2,3-Dibromopyridine, the common compound, a new synthetic route is introduced below. Quality Control of 2,3-Dibromopyridine

General procedure: A mixture of MeCN and MeOH (2:1, 15 ml) wasadded to a mixture of 2,3-dibromopyridine (1) (474 mg,2.0 mmol), arylboronic acid (2.1 mmol), K2CO3 (560 mg,4.0 mmol), PPh3 (52 mg, 10 mol %) and Pd(OAc)2 (23 mg,5 mol %) in a screw-cap vial. Reaction mixture was flushedwith argon, sealed, and stirred at 50C for 24 h in an oilbath. Then the reaction mixture was cooled to room temperature and filtered through Celite. Filtrate was concentratedunder reduced pressure, the residue was dissolved in CH2Cl2(20 ml), washed with water (3×10 ml) and dried overNa2SO4. Solvent was evaporated under reduced pressure,and the residue was purified by column chromatography on silica (hexane-EtOAc, 30:1) to provide pure pyridines 2a-j. 3-Bromo-2-phenylpyridine (2a).53 Yield 387 mg(83%), colorless oil.

The synthetic route of 13534-89-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Shestakov, Aleksandr N.; Pankova, Alena S.; Kuznetsov, Mikhail A.; Chemistry of Heterocyclic Compounds; vol. 53; 10; (2017); p. 1103 – 1113; Khim. Geterotsikl. Soedin.; vol. 53; 10; (2017); p. 1103 – 1113,11;,
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. 959616-64-9, name is Methyl 2-chloro-5-fluoro-6-methoxynicotinate, molecular formula is C8H7ClFNO3, 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. name: Methyl 2-chloro-5-fluoro-6-methoxynicotinate

A mixture of methyl 2-chloro-5-fluoro-6-methoxy-pyridine-3-carboxylate (200 mg, 0.911 mmol), 4-fluoro-2-methoxyphenol (114 pL, 1.00 mmol) and cesium carbonate (742 mg, 2.28 mmol) in MeCN (8 mL) was stirred at 80 C for 3 h, then allowed to cool to room temperature with stirring. Water (30 mL) and methanol (5 mL) were added and the resulting mixture was sonicated briefly then stirred for 4 h. The precipitate was collected by filtration, washed with water and dried under vacuum to give methyl 5-fluoro-2-(4-fluoro-2-methoxy-phenoxy)-6-methoxy- pyridine-3-carboxylate (237 mg, 0.727 mmol, 79.9% yield) as a beige solid. MS, ES+m/z 326.0 [M+H]+. -NMR (400 MHz, DMSO-rie) d 8.12 (d, J=l0.11 Hz, 1 H), 7.18 (dd, J=8.72, 5.94 Hz, 1 H), 7.09 (dd, J=l0.74, 2.91 Hz, 1 H), 6.81 (td, J=8.46, 2.78 Hz, 1 H), 3.83 (s, 3 H), 3.72 (s, 3 H), 3.57 (s, 3 H).

With the rapid development of chemical substances, we look forward to future research findings about 959616-64-9.

Reference:
Patent; LIEBER INSTITUTE, INC.; HUANG, Yifang; POSLUSNEY, Michael; ERNST, Glen; BARROW, James; (0 pag.)WO2020/14246; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 153034-94-7 , The common heterocyclic compound, 153034-94-7, name is 2-Fluoro-4-iodo-5-picoline, molecular formula is C6H5FIN, 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.

Step 1: ethyl 4-(2-chlorophenyl)-1-(2-fluoro-5-methylpyridin-4-yl)-1H-pyrrole-3-carboxylate To a slurry of copper(I) iodide (0.14 g, 0.73 mmol) and potassium carbonate (3.03 g, 21.9 mmol) in 1,4-dioxane (15 mL) were added 2-fluoro-4-iodo-5-methylpyridine (5.03 g, 21.2 mmol), ethyl 4-(2-chlorophenyl)-1H-pyrrole-3-carboxylate (0.95 g, 3.8 mmol), and trans-N,N’-dimethylcyclohexane-1,2-diamine (0.23 mL, 1.46 mmol). The reaction mixture was allowed to stir in a sealed vial for 48 h at 105 C. and then allowed to cool to rt. The mixture was diluted with EtOAc and washed with brine. The organic solutions were combined, concentrated, and purified by column chromatography to give ethyl 4-(2-chlorophenyl)-1-(2-fluoro-5-methylpyridin-4-yl)-1H-pyrrole-3-carboxylate (1.2 g, 88%). LCMS (FA): m/z=359.3 (M+H).

The synthetic route of 153034-94-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; Chau, Ryan W.; Cullis, Courtney A.; Duffey, Matthew O.; Gipson, Krista E.; Hu, Yongbo; Li, Gang; Sintchak, Michael D.; Vos, Tricia J.; US2013/165464; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 153034-86-7, 2-Chloro-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: C5H3ClIN, blongs to pyridine-derivatives compound. Formula: C5H3ClIN

l-Bromo-3-ethynylbenzene (3.76 g, 20.77 mmol), palladium(II) dicMorobis(triphenylphosphine) (73 mg, 0.10 mmol) and copper(I) iodide (0.020 g, 0.10 mmol) were dissolved in anhydrous tetrahydrofuran (15 mL) and triethylamine (10 mL). 2- Chloro-4-iodorhoyridine (4.97 g, 20.77 mmol) dissolved in anhydrous tetrahydrofuran (5 mL) was added. The reaction was stirred at room temperature over night under an atmosphere of nitrogen. The reaction was quenched with hydrochloric acid (2M aq.) and extracted with dichloromethane twice. The aquous phase was then made basic using NaOH (15% aq.) and extracted with dichloromethane twice. The combined organic phases were concentrated in vacuo and the product was purified by column chromatography using a gradient eluent (0 to 30% ethyl acetate in heptane) to give 5.38 g (89% yield) of the title compound: MS (ESI) m/z 294 [M+l]+

At the same time, in my other blogs, there are other synthetic methods of this type of compound,153034-86-7, 2-Chloro-4-iodopyridine, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; ASTEX THERAPEUTICS LTD; WO2008/76046; (2008); 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. 138006-41-4, name is 3-Bromo-2,5-dichloropyridine, the common compound, a new synthetic route is introduced below. Computed Properties of C5H2BrCl2N

Step Ml. A mixture of tert-butyl piperazine- l-carboxylate (186 mg, 0.996 mmol), 3-bromo- 2,5-dichloropyridine (226mg, 0.996 mmol), and DIEA (174 muEpsilon, 0.996 mmol) in NMP was heated at 160-165 C for 15 min. Silica gel column purification with 5% EtOAc in DCM gave tert-butyl 4-(3-bromo-5-chloropyridin-2-yl)piperazine-l-carboxylate (204mg, 0.542 mmol, 54.4 % yield). White solid. ^- MRCCDCls, 500MHz) delta 8.18 (1H, s), 7.80 (1H, s), 3.58 (4H,m), 3.26(4H,m), 1.49 (9H, s),

The synthetic route of 138006-41-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; CIANCI, Christopher W.; GERRITZ, Samuel; KIM, Sean; LANGLEY, David R.; LI, Guo; PEARCE, Bradley C.; PENDRI, Annapurna; SHI, Shuhao; ZHAI, Weixu; ZHU, Shirong; WO2012/44531; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 31872-63-6, 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 31872-63-6, name is 3-Bromo-4-chloro-5-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows.

3-bromo-4-methyl-5-nitropyridine (94a) Diethyl malonate (3.84 mL, 25.3 mmol) was slowly added to a suspension of sodium hydride (1.01 g of a 60% suspension in oil, 25.3 mmol) in DMF (15 mL) at 0 C. and stirred 30 min until gas evolution ceased. 3-bromo-4-chloro-5-nitropyridine (3.00 g, 12.6 mmol) was added slowly, and the dark reddish-brown solution was stirred at room temperature for 1 hour. The reaction was carefully quenched with water and acidified to pH 1 with 1N HCl. The aqueous mixture was extracted with EtOAc (2*150 mL). The combined organics were washed with water (100 mL) and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The residue was diluted with 4N HCl (50 mL) and the solution refluxed 16 hours. The mixture was cooled in an ice bath and basified to pH 7 with 50% NaOH. The aqueous mixture was extracted with EtOAc (3*100 mL) and the combined organics were washed with brine, dried (MgSO4), filtered and concentrated in vacuo to afford 94a (1.90 g, 70%) as a yellow solid. 1H NMR (300 MHz, CDCl3) delta 8.94 (s,1H), 8.97 (s,1H), 2.65 (s, 3H).

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 31872-63-6, 3-Bromo-4-chloro-5-nitropyridine.

Reference:
Patent; PFIZER INC; US2005/90529; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem