Tag: M.W:100-200

Application of 10128-91-3, Adding some certain compound to certain chemical reactions, such as: 10128-91-3, name is Methyl 2-oxo-1,2-dihydro-3-pyridinecarboxylate,molecular formula is C7H7NO3, 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 10128-91-3.

Methyl 2-hydroxynicotinate (500 mg, 3.27 mmol) and N-bromosuccinimide (756 mg, 4.25 mmol) were dissolved in dichloromethane and the mixture was stirred at 50 C for 48 hours. The mixture was cooled to room temperature and then concentrated under reduced pressure. The resulting residue was filtered with a small amount of dichloromethane to obtain the title compound (0.3 g, yield: 40%, yellow solid). *H NMR (500MHz, DMSO-d6) d 8.07 (d, J = 5.0 Hz, 1H), 7.98 (d, J = 5.0 Hz, 1H), 3.75 (s, 3H)

According to the analysis of related databases, 10128-91-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; WELLMARKER BIO CO., LTD.; LEE, Hyunho; PARK, Chun-Ho; HUR, Sun Chul; MOON, Jai-Hee; SHIN, Jae-Sik; HONG, Seung-Woo; PARK, Yoon-Sun; KIM, Joseph; LEE, Sohee; KIM, Hyojin; PARK, Hyebin; (83 pag.)WO2019/182274; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 878207-92-2, 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.878207-92-2, name is Methyl 6-chloro-3-methylpicolinate, molecular formula is C8H8ClNO2, molecular weight is 185.61, as common compound, the synthetic route is as follows.

To a stirred solution of methyl 6-chloro-3-methylpicolinate (1.0 g, 5.4 mmol) in 1,4-Dioxane (20 mL) were added, 2-(3-((4-Methoxybenzyl)oxy)-5-(trifluoromethyl)phenyl)-4,4,5,5-tetra methyl- 1, 3, 2-dioxaborolane (3.5 g, 8.6 mmol), Na2C03 (1.7 g, 16.2 mmol) in H20 (2 mL) and the mixture was degassed for 10 mins. To this, PdCl2(dppf) (0.16 g, 0.22 mmol) was added and the reaction mixture was heated to 100 C overnight. After completion (TLC), it was diluted with Ethyl acetate (50 mL) and filtered through a pad of celite. The filtrate was collected, concentrated and purified by flash chromatography using Ethyl acetate: Hexanes to afford the titled compound (1.2 g, 51%) as white solid.

The chemical industry reduces the impact on the environment during synthesis 878207-92-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; LUPIN LIMITED; MADAN, Sachin; TALE, Prashant, Vitthalrao; ZADE, Seema, Prabhakar; PATIL, Amolsing, Dattu; KULKARNI, Sanjeev, Anant; PALLE, Venkata, P.; KAMBOJ, Rajender, Kumar; WO2015/162538; (2015); 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. 183208-35-7, name is 5-Bromo-1H-pyrrolo[2,3-b]pyridine, molecular formula is C7H5BrN2, 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-1H-pyrrolo[2,3-b]pyridine

General procedure: To a solution of appropriate pyrrolo-pyridines 8a-f (2.5 mmol) in 10 mL of anhydrous DCM, anhydrous AlCl3 (1.2 g, 8.8 mmol) was slowly added. The reaction mixture was heated under reflux and BrCOCH2Br (2.5 mmol, 0.2 mL) in 2 mL of anhydrous DCM was added dropwise. The resulting solution was allowed to stir under reflux for 40 min. After cooling, water and ice were slowly added and the obtained precipitate (for derivative 9a) was filtered off or the oil residue (for derivatives 9b-f) was extracted with DCM (3 × 20 mL) and purified by column chromatography using DCM/ethyl acetate (9/1) as eluent [42].

With the rapid development of chemical substances, we look forward to future research findings about 183208-35-7.

Reference:
Article; Carbone, Anna; Parrino, Barbara; Vita, Gloria Di; Attanzio, Alessandro; Span, Virginia; Montalbano, Alessandra; Barraja, Paola; Tesoriere, Luisa; Livrea, Maria Antonia; Diana, Patrizia; Cirrincione, Girolamo; Marine Drugs; vol. 13; 1; (2015); p. 460 – 492;,
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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. 6937-03-7, name is Methyl 2-aminoisonicotinate, the common compound, a new synthetic route is introduced below. Formula: C7H8N2O2

Preparation of compound 24a: imidazo[1,2-a]pyridine-7-carboxylic acid methyl esterTo a solution of 2-Bromo-1 ,1 -diethoxy-ethane (18.62 g, 0.095 mol) in H2O (80 ml) was added aq. HBr (2 ml). The resulting mixture was heated to 80 0C for 1.5 h and then was cooled to 40 0C. Then a solution of 2-Amino-isonicotinic acid methyl ester(9.61 g, 0.063 mol) and NaHCO3 (6.615 g, 0.0788 mol) in CH3OH/ H2O (3:1 400 ml) was added dropwise to the above mixture. The resulting mixture was heated to 80 0C for 18 h. The mixture was concentrated and cooled to room temperature, and the solid was collected by filtration and dried in vacuo which gave the title compound 24a as a yellow solid (9.5 g, 85.7%).

The synthetic route of 6937-03-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; NINKOVIC, Sacha; BRAGANZA, John Frederick; COLLINS, Michael Raymond; KATH, John Charles; LI, Hui; RICHTER, Daniel Tyler; WO2010/16005; (2010); 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. 15128-89-9, name is 3-Hydroxy-4-methyl-2-nitropyridine. A new synthetic method of this compound is introduced below., category: pyridine-derivatives

To a solution of 4-methyl-2-nitropyridin-3-ol (4.85 g) in methanol (90 mL) was added 28% sodium methoxide solution in methanol (6.3 mL) . The solution was stirred at room temperature for 15 min and then cooled with an ice-bath. A solution of bromine (1.6 mL) in methanol (15 mL) was added dropwise, and the reaction mixture was stirred at 00C for 2 hr and concentrated to give crude 6-bromo-4-methyl-2- nitropyridin-3-ol, which was used for the next step without further purification. To a mixture of crude 6-bromo-4- methyl-2-nitropyridin-3-ol and potassium carbonate (8.70 g) in acetone (70 mL) was added ethyl bromoacetate (3.5 mL) . The mixture was refluxed for 15 hr and the solvent was evaporated. DMSO (50 mL) , potassium carbonate (5.00 g) and ethyl bromoacetate (1.5 mL) were additionally added, and the mixture was stirred at room temperature for 60 hr, poured into water and extracted with ethyl acetate. The extract was washed with 5% aqueous Na2S2O3, water and saturated aqueous NaHCO3, dried over MgSO and concentrated. The residue was chromatographed on silica gel using n- hexane/ethyl acetate as an eluent to give the title compound as an oil (7.40 g) .1H-NMR (300 MHz, CDCl3) delta: 1.31 (t, J = 6.6 Hz, 3H), 2.47 (s, 3H), 4.27 (q, J = 6.6 Hz, 2H), 4.60 (s, 2H), 7.59 (s, IH).

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, 15128-89-9, 3-Hydroxy-4-methyl-2-nitropyridine.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2007/77961; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 21427-62-3, 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 21427-62-3 as follows.

To a solution of 129.2 g (0.69 mol) of 2,5-dichloro-3-nitropyridine in 1300 ml of dioxane is added 26 0 g of Raney-nickel, that has previously been washed with ethanol. This mixture is then hydrogenated with hydrogen under normal pressure at 20-35 C. After uptake of 20% of the theoretical amount of hydrogen, another 30 g of washed Raney-nickel catalyst are added. After hydrogenating for 22 hours, the catalyst is filtered off, the solvent is evaporated and the residue is crystallized from hexane/ ethyl acetate. Thus, 84.9 g of 3-amino-2,5-dichloropyridine (78% of the theory) are obtained, which melts at 129-132 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,21427-62-3, its application will become more common.

Reference:
Patent; Ciba-Geigy Corporation; US4935051; (1990); 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.1150617-54-1, name is 6-Bromo-1H-pyrazolo[4,3-b]pyridine, molecular formula is C6H4BrN3, molecular weight is 198.02, as common compound, the synthetic route is as follows.Formula: C6H4BrN3

6-bromo-1H-pyrazolo[4,3-b]pyridine (400 mg, 2.0 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (500 mg, 2.4 mmol), K2CO3 (828 mg, 6 mmol), and Pd(dppf)Cl2(81.7 mg, 0.1 mmol) were dissolved in the solvent of 1,4-dioxane/H2O (v/v = 3:1, 20 mL). The resultingmixture was stirred at 80 C under Ar for 2 h. Then, the reaction mixture was evaporated to dryness.The residue was purified by flash chromatography to give compound 39 as a yellow hairy solidwith the yield of 82%. 1H-NMR (300 MHz, DMSO-d6, ppm) 13.29 (s, 1H), 8.80 (s, 1H), 8.36 (s, 1H),8.24 (s, 1H), 8.07 (s, 2H), 3.90 (s, 3H). ESI-MS: C10H10N7O2S, Exact Mass: 199.09, m/z 200.0 (M + 1)+.Retention time 2.51 min, >95% purity.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1150617-54-1, 6-Bromo-1H-pyrazolo[4,3-b]pyridine, and friends who are interested can also refer to it.

Reference:
Article; Jiang, Alan; Liu, Qiufeng; Wang, Ruifeng; Wei, Peng; Dai, Yang; Wang, Xin; Xu, Yechun; Ma, Yuchi; Ai, Jing; Shen, Jingkang; Ding, Jian; Xiong, Bing; Molecules; vol. 23; 3; (2018);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 154237-70-4, Adding some certain compound to certain chemical reactions, such as: 154237-70-4, name is 4-Bromo-3-cyanopyridine,molecular formula is C6H3BrN2, 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 154237-70-4.

Step 3, Method 15: 4-[5-(2-Fluoroethoxy)-l-benzofuran-2-yl]pyridine-3- carbonitrile[0204] To a stirred solution of [5-(2-fluoroethoxy)-l-benzofuran-2-yl]boronic acid (120 mg, 0.54 mmol) and 4-bromo-3-cyanopyridine (98 mg, 0.54 mmol) in 1,4- dioxane (3 mL) under nitrogen were added copper(I) iodide (10 mg, 0.054 mmol), caesium fluoride (163 mg, 1.07 mmol) and tetrakis(triphenylphosphine)palladium(0) (31 mg, 0.027 mmol). The reaction mixture was degassed using a stream of nitrogen for 10 minutes then heated under a nitrogen atmosphere to 60 C and stirred for 18 hours. The mixture was concentrated, ethyl acetate (10 mL) and water (10 mL) added and the layers separated. The organic layer was washed with water (2 x 10 mL), brine (2 x 10 mL), dried over magnesium sulphate, filtered and concentrated. Purification by FCC (silica, 0-30% ethyl acetate in heptane) and recrystallisation from heptane- dichloromethane (5:2) gave the title compound 46 mg (30% yield) as a yellow solid. Example 1, Method 15: 4-[5-(2-Fluoroethoxy)-l-benzofuran-2-yl]pyridine-3- carbonitrile[0205] 5H MR (500 MHz, DMSO) 9.11 (s, 1H), 8.92 (d, J= 5.4 Hz, 1H), 8.07 (d, J = 5.4 Hz, 1H), 7.93 (s, 1H), 7.64 (d, J= 9.0 Hz, 1H), 7.40 (d, J= 2.4 Hz, 1H), 7.13 (dd, J= 9.0, 2.5 Hz, 1H), 4.78 (dt, J = 47.9, 3.8 Hz, 2H), 4.30 (dt, J = 30.1, 3.7 Hz, 2H). Tr(MET-uHPLC-AB-lOl) = 3.21 min, (ES+) (M+H)+283.

According to the analysis of related databases, 154237-70-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CHDI FOUNDATION, INC.; DOMINGUEZ, Celia; WITYAK, John; BARD, Jonathan; BROWN, Christopher, John; PRIME, Michael, Edward; WEDDELL, Derek, Alexander; WALTER, Daryl, Simon; GILES, Paul, Richard; WIGGINTON, Ian, James; TAYLOR, Malcolm, George; GALAN, Sebastien, Rene, Gabriel; JOHNSON, Peter, David; KRUeLLE, Thomas, Martin; MORAO, Inaki; CLARK-FREW, Daniel; SCHAERTL, Sabine; HERRMANN, Frank; GRIMM, Steffen, Kaspar; KAHMANN, Jan, Dirk; SCHEICH, Christoph; (120 pag.)WO2016/33460; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 13472-58-7, 3,5-Dichloro-2-methoxypyridine, 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, Application In Synthesis of 3,5-Dichloro-2-methoxypyridine, blongs to pyridine-derivatives compound. Application In Synthesis of 3,5-Dichloro-2-methoxypyridine

A solution of 3,5-dichloro-2-methoxypyridine (16 g, 90 mmol) in THF(100 mL) was slowly added to a solution of LDA (53.9 ml, 108 mmol) (2M in THF) at -78 C. DMF (14 mL, 180 mmol) was added to the reaction mixture and the resulting solution stirred at -78 C for about lh. The reaction mixture was then poured into a NH4C1 saturated aqueous solution. The aqueous layer was extracted with EtOAc (3 x 20 mL). The combined organic portion was dried over anhydrous Na2S04, filtered, and concentrated under reduced pressure to give 3,5-dichloro-2-methoxyisonicotinaldehyde (17.54 g, 90 % ). LC/MS (Table 1, Method d) Rt = 1.86 min.; MS m/z: 205, 207 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,13472-58-7, 3,5-Dichloro-2-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; ABBVIE INC.; ARGIRIADI, Maria A.; BREINLINGER, Eric; CUSACK, Kevin P.; HOBSON, Adrian, D.; POTIN, Dominique; BARTH, Martine; AMAUDRUT, Jerome; POUPARDIN, Olivia; MOUNIER, Laurent; KORT, Michael, E.; (392 pag.)WO2016/198908; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 886364-86-9, 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. 886364-86-9, name is 5-Bromo-4-methylpicolinonitrile. A new synthetic method of this compound is introduced below.

A mixture of (±)-trans-N-(6-bromo-8-chloroisoquinolin-3-yl)-2-cyanocyclopropane-1-carboxamide (125 mg, 0.571 mmol), bis(pinacolato)diboron (222 mg, 0.856 mmol), potassium acetate (168 mg, 1.711 mmol), and Pd(dppf)Cl2 (42.2 mg, 0.0571 mmol) in 1,4-dioxane (3 mL) was heated in a microwave at 130 C. for 45 minutes to give (±)-(8-chloro-3-((trans-2-cyanocyclopropane-1-carboxamido)isoquinolin-6-yl)boronic acid. LCMS (ESI): [M+H]+=316.0. (0975) 5-Bromo-4-methylpicolinonitrile (168 mg, 0.856 mmol) and sodium carbonate (1 mol/L) in water (2.85 ml, 2.852 mmol) were then added. The reaction mixture was heated in a microwave at 90 C. for 55 minutes. The organic layer was purified with silica gel column chromatography (0.5 to 9% methanol in dichloromethane) to give (±)-(trans-N-(8-chloro-6-(6-cyano-4-methylpyridin-3-yl)isoquinolin-3-yl)-2-cyanocyclopropane-1-carboxamide (187 mg, 86.5% yield). LCMS (ESI) [M+H]+=388.0.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,886364-86-9, 5-Bromo-4-methylpicolinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Genentech, Inc.; Chan, Bryan; Drobnick, Joy; Gazzard, Lewis; Heffron, Timothy; Liang, Jun; Malhotra, Sushant; Mendonca, Rohan; Rajapaksa, Naomi; Stivala, Craig; Tellis, John; Wang, Weiru; Wei, BinQing; Zhou, Aihe; Cartwright, Matthew W.; Lainchbury, Michael; Gancia, Emanuela; Seward, Eileen; Madin, Andrew; Favor, David; Fong, Kin Chiu; Hu, Yonghan; Good, Andrew; US2018/282282; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem