Category: 13466-38-1

Reference of 13466-38-1 ,Some common heterocyclic compound, 13466-38-1, molecular formula is C5H4BrNO, 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.

To a stirred solution of 5-bromopyridin-2-ol (10 g, 57.5 mmol) in anhydrous THF (200 ml) at RT was added hydroxypivalic acid methyl ester (9.16 ml, 71.8 mmol).Triphenylphosphine (18.8 g, 71.8 mmol) was then added followed by dropwise addition ofdiisopropyl azodicarboxylate (14.1 ml, 71.8 mmol) at OoC. The reaction was then heated to 55C and allowed to stir at this temperature over night. The reaction mixture was concentrated. The residue was treated with EtOAc (70 ml) and then Hexane (70 ml), the solid was filtered off. The filtrate was concentrated, separated by MPLC (10-100% EtoAC in hexane) to give methyl 3-(5-bromopyridin-2-yloxy)-2,2-dimethylpropanoate (9.94 g). LC-MS (ES, mlz) C11H14BrNO3: 287; Found: 288 [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. 13466-38-1, 5-Bromopyridin-2-ol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DEVITA, Robert, J.; YU, Yang; LIU, Jian; HE, Shuwen; KRIKORIAN, Arto, D.; MILLER, Daniel, J.; WU, Zhicai; YANG, Ginger Xu-Qiang; HONG, Quingmei; LAI, Zhong; ZORN, Nicolas; TING, Pauline, C.; WO2013/130370; (2013); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 13466-38-1, Adding some certain compound to certain chemical reactions, such as: 13466-38-1, name is 5-Bromopyridin-2-ol,molecular formula is C5H4BrNO, 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 13466-38-1.

(i) 5-bromo-l-ethylpyridin-2(lH)-onePotassium tert-butoxide (328 mg) was added to 5-bromopyridin-2(lH)-one (509 mg) in dimethoxyethane (15 mL) at 20C under an atmosphere of nitrogen and stirred for 30 min. Potassium carbonate (283 mg) and iodoethane (0.236 mL) were added to the reaction mixture and the resulting suspension was stirred at 95C for 3 h. The reaction mixture was cooled and filtered, evaporated to dryness and redissolved in dichloromethane, and washed with 0.1M hydrochloric acid. The organic layer was dried over magnesium sulfate, filtered and evaporated to afford an oil which was purified by chromatography on silica eluting with 30 to 50% ethyl acetate in z’sohexane. Pure fractions were evaporated to dryness to afford the subtitled compound (367 mg).1H NMR (500 MHz, DMSO) delta 8.04 (d, IH), 7.50 (dt, IH), 6.35 (d, IH), 3.88 (q, 2H), 1.19 (t, 3H). m/e (APCI+) 204 [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. 13466-38-1, 5-Bromopyridin-2-ol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; FORD, Rhonan; KINCHIN, Elizabeth; MATHER, Andrew; METE, Antonio; MILLICHIP, Ian; STANIER, Andrew Geoffrey; WO2011/154677; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 13466-38-1, 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. 13466-38-1, name is 5-Bromopyridin-2-ol. A new synthetic method of this compound is introduced below.

Example 142 To a solution of 5-bromopyridin-2-ol (1.0 g, 5.75 mmol) in DMF (10 mL) at RT, potassium tert-butoxide (0.68 g, 6.07 mmol) was added and the mixture was stirred for 30 min. To this mixture, (bromomethyl)cyclopropane (1.03 g, 8.62 mmol) was added, and the resulting mixture was stirred at 70 C. for 2 h. The mixture was allowed to cool to RT, diluted with EtOAc (50 mL) and quenched with water (20 mL). The organic layer was washed with water (2*20 mL) and brine (20 mL), dried over anhydrous MgSO4 and filtered. The filtrate was concentrated in vacuo to afford 5-bromo-1-(cyclopropylmethyl)pyridin-2(1H)-one. 1-(Cyclopropylmethyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-one was prepared in analogous fashion to Example 140, except 5-bromo-1-(cyclopropylmethyl)pyridin-2(1H)-one was used in place of 5-bromo-1-ethylpyridin-2(1H)-one. Compound 232 was prepared from compound 8 in analogous fashion to Example 140, except 1-(cyclopropylmethyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-one was used in place of 1-ethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-one. ESI-MS m/z: 530.3 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13466-38-1, its application will become more common.

Reference:
Patent; INTELLKINE, LLC; INFINITY PHARMACEUTICALS, INC.; CASTRO, Alfredo C.; EVANS, Catherine A.; JANARDANANNAIR, Somarajannair; LESCARBEAU, Andre; LIU, Tao; SNYDER, Daniel A.; TREMBLAY, Martin R.; REN, Pingda; LIU, Yi; LI, Liansheng; CHAN, Katrina; US2013/53362; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 13466-38-1, 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 13466-38-1, name is 5-Bromopyridin-2-ol. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 5-bromopyridin-2-ol (1 g, 5.75 mmol), ClCF2COONa (0.876 g, 5.75 mmol), Cs2CO3 (2.81 g, 8.62 mmol) in DMF (20 mL) was heated at 100oC for 3h. LCMS indicated that the desired compound was formed.40 mL of water and 40 mL of EA were added to the reaction mixture. The organic phase was separated, washed with water(20 mL), brine(20 mL), dried over Na2SO4, filtered and concentrated under vacuum to give a residue, which was purified by silica gel chromatography (PE/EA=100/1) to give the title compound as a colorless oil (0.3g, 23.30%).

According to the analysis of related databases, 13466-38-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; EDGEWISE THERAPEUTICS, INC.; HUNT, Kevin; KOCH, Kevin; RUSSELL, Alan; SCHLACHTER, Stephen; WINSHIP, Paul; STEELE, Chris; UZOHO, Grace; (219 pag.)WO2020/97265; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 13466-38-1, Adding some certain compound to certain chemical reactions, such as: 13466-38-1, name is 5-Bromopyridin-2-ol,molecular formula is C5H4BrNO, 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 13466-38-1.

A mixture of 5-bromo-1, 2, 5, 6-tetrahydropyridin-2-one (3.0 g, 17.0 mmol, 1.0 equiv) and Cs 2CO 3 (16.7 g, 51.3 mmol, 3.0 equiv) in DMF was stirred for 5 min at room temperature under nitrogen atmosphere. To the above mixture was added iodoethane (8.0 g, 51.3 mmol, 3.0 equiv) dropwise over 5 min at room temperature. The resulting mixture was stirred for additional 40 min at room temperature. The residue was purified by Prep-TLC (PE/EtOAc 5: 1) to afford 5-bromo-1-ethyl-1, 2, 5, 6-tetrahydropyridin-2-one (1.4 g, 41.7%) as a light yellow solid. LCMS: m/z (ESI), [M+H] + = 202.1.

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. 13466-38-1, 5-Bromopyridin-2-ol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; DIZAL (JIANGSU) PHARMACEUTICAL CO., LTD.; ZENG, Qingbei; QI, Changhe; TSUI, Honchung; YANG, Zhenfan; ZHANG, Xiaolin; (206 pag.)WO2020/52631; (2020); 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. 13466-38-1, name is 5-Bromopyridin-2-ol. A new synthetic method of this compound is introduced below., Formula: C5H4BrNO

Synthesis of 5-bromo-2-(2-methoxyethoxy)pyridineTo a solution of 5-bromopyridin-2-ol (5.75 mmol, lg), triphenylphosphine (8.62mmol, 2.26 g), and 2-methoxyethanol (7.2 mmol, 0.55 g) in THF (25 mL), was added slowly diisopropyl azodicarboxylate (8.62 mmol, 1.7 mL) at RT. The mixture was stirred at RT overnight. The reaction was quenched with MeOH, diluted with water and extracted with DCM (25 mL). The organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated in vacuo. Crude was purified by flash chromatography (cyclohexane/EtOAc = 9/2 -> 7/3) to yield title product. Y: 1.05 g (79%), P>80%, rt=3.9 min (gradient A), (M+H)+ = 233.

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, 13466-38-1, 5-Bromopyridin-2-ol.

Reference:
Patent; EUROSCREEN S.A.; HOVEYDA, Hamid; DUTHEUIL, Guillaume; EL BOUSMAQUI, Mohamed; BERNARD, Jerome; WO2011/151434; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 13466-38-1 , The common heterocyclic compound, 13466-38-1, name is 5-Bromopyridin-2-ol, molecular formula is C5H4BrNO, 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.

4.43g (0.0200ml) of N-(4-fluorobenzyl)-1-oxa-6-azaspiro[2,5]-octane and 3.55g (0.0202mol) of 5-bromo-2-hydroxy- pyridine were weighed and added into 40mL of N,N-dimethylformamide, and then 0.15g (0.0011mol) of potassium carbonate was added. The reaction was stirred and reacted at a bath temperature of about 80C for 1 day and the solvent was recovered under reduced pressure. Potassium carbonate aqueous solution was added to the residue and the mixture was extracted with dichloromethane twice, combined, washed with water and dried, and the solvent was recovered. The residue was crystallized with petroleum ether-ethyl acetate to obtain a colorless flake-like crystal, 2.65g, yield 33.2%. Melting point: 181-183C. 1H-NMR (CDCl3, ppm) delta: 7.419 (1H, s), 7.405 (1H, dd, J1 = 9.80 Hz, J2 = 2.52 Hz), 7.252 (1H, t, J = 8.68 Hz), 6.990 (2H, t, J = 8.68 Hz), 6.547 (1H, d, J = 9.80 Hz,), 4.000 (2H, s), 3.864 (1H, s), 3.480 (2H, s), 2.641 (2H, dd, J1 = 7.84 Hz, J2 = 3.92 Hz), 2.352 (2H, t3d, J1 = 9.84 Hz, J2 = 1.96 Hz), 1.53-1.73 (4H, m). 2.65g of free base was weighed, heated and dissolved in ethanol-ethyl acetate, salified with HCl-EtOH while warm and naturally cooled to obtain a colorless fine granular crystal, which was dried under vacuum to obtain 2.29g product. Melting point: 255-257C, yield: 80%.

The synthetic route of 13466-38-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Institute Of Pharmacology And Toxicology Academy Of Military Medical Sciences P.L.A. China; LI, Yunfeng; YANG, Rifang; ZHANG, Youzhi; LI, Yongzhen; JIN, Zengling; LI, Peng; YUAN, Li; YUN, Liuhong; ZHAO, Nan; ZHANG, Cheng; XU, Xiaodan; ZHAO, Rusheng; CHEN, Hongxia; XUE, Rui; QIN, Juanjuan; WANG, Zhenzhen; YAO, Jiazhi; EP2570410; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 13466-38-1, 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. 13466-38-1, name is 5-Bromopyridin-2-ol, molecular formula is C5H4BrNO, 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.

termediate 17 ethyl trans-4-[(“5-bromopyridin-2-yl oxylcvclohexanecarboxylate To a mixture of 5-bromo-2-hydroxypyridine (11 g, 63.2 mmol), ethyl cis-4- hydroxycyclohexanecarboxylate (13.61 g, 79 mmol) and triphenylphosphine (20.73 g, 79 mmol) in THF (250 ml) at room temperature added diisopropyl azodicarboxylate (15.98 g, 79 mmol) dropwise, after that, the reaction mixture Was stirred overnight a at 55C for two days under N2. The reaction mixture was cooled to room temperature, then concentrated under vacuum. The residue was dissolved in 100 mL of ethyl acetate, then 100 mL hexane added. Stirred over night. The mixture was filtered and concentrated, the residue was purified by a silica gel column and eluted with ethyl acetate/hexane 0-50%. This resulted in ethyl trans-4- [(5-bromopyridin-2-yl)oxy]cyclohexanecarboxylate as a white solid. LC-MS (ES, m/z) C14H18BrN03: 327; Found: 328 [M+H]+.

According to the analysis of related databases, 13466-38-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DEVITA, Robert, J.; HE, Shuwen; LIU, Jian; CERNAK, Timothy, A.; KRIKORIAN, Arto, D.; YANG, Ginger XuQiang; WU, Zhicai; YU, Yang; SHEN, Dong-Ming; LAI, Zhong; HONG, Qingmei; NARGUND, Ravi, P.; WO2013/96093; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 13466-38-1, 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. 13466-38-1, name is 5-Bromopyridin-2-ol, molecular formula is C5H4BrNO, 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.

Example 140 To a suspension of NaH (60% dispersion in mineral oil, 1.34 g, 0.056 mol) in THF (10 mL), a solution of 5-bromopyridin-2-ol (2.5 g, 0.014 mol) in THF (50 mL) was added and the resulting mixture was stirred at RT for 1 h. To this mixture, iodoethane (10.9 g, 0.07 mol) was added and the mixture was stirred at RT overnight. The mixture was quenched with water and washed with NH4Cl solution. The organic phase was separated, then concentrated in vacuo and the residue was purified by flash chromatography on silica gel (50-100% PE-AE) to afford 5-bromo-1-ethylpyridin-2(1H)-one.

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 13466-38-1, 5-Bromopyridin-2-ol.

Reference:
Patent; INTELLKINE, LLC; INFINITY PHARMACEUTICALS, INC.; CASTRO, Alfredo C.; EVANS, Catherine A.; JANARDANANNAIR, Somarajannair; LESCARBEAU, Andre; LIU, Tao; SNYDER, Daniel A.; TREMBLAY, Martin R.; REN, Pingda; LIU, Yi; LI, Liansheng; CHAN, Katrina; US2013/53362; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 13466-38-1, 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.13466-38-1, name is 5-Bromopyridin-2-ol, molecular formula is C5H4BrNO, molecular weight is 173.9954, as common compound, the synthetic route is as follows.

To a solution of 5-bromopyridin-2-ol (1 g, 5.75 mmol) in DMF (10 mL) were added 2-iodopropane (4.9 g, 28.75 mmol) and K2CO3 (4 g, 28.75 mmol). The mixture was stirred at rt overnight. The mixture was diluted with water (20 mL) extracted with EtOAc (3×25 mL), the combined organic phase was washed with brine, dried over Na2SO4, concentrated and purified by prep TLC to give 5-bromo-1-isopropylpyridin-2(1H)-one (380 mg, 31%). 1H NMR (CDCl3): 1.35 (d, 6H), 5.65-5.75 (m, 1H), 6.48 (d, 1H), 7.30 (m, 1H), 7.41 (d, 1H).

The chemical industry reduces the impact on the environment during synthesis 13466-38-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Vitae Pharmaceuticals, Inc.; Boehringer Ingelheim International GmbH; US2010/331320; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem