Category: 1003-68-5

Electric Literature of 1003-68-5 ,Some common heterocyclic compound, 1003-68-5, molecular formula is C6H7NO, 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 5-methylpyridin-2(lH)-one, 1-495 (cas: 1003-68-5, 5.0 g, 45.87 mmol, 1.0 equiv.), KI (1.522 g, 9.17 mmol, 0.2 equiv.), and NaH (60%, 2.20 g, 55.04 mmol, 1.2 equiv.) in DMF (20 ml) was stirred under nitrogen at 0 C for 1 hour. Then the reaction mixture was added to a solution of /er/-butyl (2-bromoethyl)carbamate (cas: 39684-80-5, 15.34 g, 68.80 mmol, 1.5 equiv.) in DMF (30 mL) dropwise. The reaction mixture was stirred at 0 C for 1 hour and then 25 C for 12 hours. LCMS analysis showed -50% conversion, at which point H20 (50 mL) was added and the reaction mixture was extracted with EtOAc (100 mL x 3). The organic phase was dried and purified by silica gel chromatography (20%-50% EtOAc with Petroleum ether) to give the product /er/-butyl (2- (5-methyl-2-oxopyridin-l(2H)-yl)ethyl)carbamate, 1-496 (1.7 g, 15% yield, 95% purity) as a white solid, MS (ESI, positive ion) m/z: 253(M+l) and byproduct: tert-butyl (2-((5- methylpyridin-2-yl)oxy)ethyl)carbamate (0.4 g, 3% yield, 95% purity), MS (ESI, positive ion) m/z: 253(M+l).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1003-68-5, its application will become more common.

Reference:
Patent; CARMOT THERAPEUTICS, INC.; ENQUIST, Johan; KRISHNAN, Shyam; ATWAL, Suman; ERLANSON, Daniel; FUCINI, Raymond V.; HANSEN, Stig; SAWAYAMA, Andrew; SETHOFER, Steven; (719 pag.)WO2019/183577; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1003-68-5 ,Some common heterocyclic compound, 1003-68-5, molecular formula is C6H7NO, 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.

Aromatic heterocyclic substrates 1s (0.1mmol), 5-methylpyridone 2b (0.15mmol), copper acetate hydrate (0.1mmol), potassium acetate (0.2mmol), DMSO (1.0mL) respectively in an air atmosphere Add to a 15mL Schlenk tube, and then directly seal the tube at 80 C for 12h. After the reaction was completed, the mixture was cooled to room temperature, and a small amount of ethyl acetate and ammonia were added to quench the reaction. The ethyl acetate was repeatedly extracted. The organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate, filtered under reduced pressure, and the solvent was evaporated under reduced pressure. The crude product was separated and purified by a preparative plate (DCM: MeOH = 35: 1) to obtain 3sb as a white solid, 23.2 mg, with a yield of 60%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1003-68-5, its application will become more common.

Reference:
Patent; Shanghai Laishi Blood Goods Co., Ltd.; Wang Peng; Yu Jinfeng; Li Jianjun; (32 pag.)CN110386929; (2019); A;,
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. 1003-68-5, name is 5-Methylpyridin-2(1H)-one. A new synthetic method of this compound is introduced below., Application In Synthesis of 5-Methylpyridin-2(1H)-one

A mixture of CuI (0.19 g, 1 mmol), Cs2CO3 (6.85 g, 20 mmol) and ethyl 2-oxocyclohexanecarboxylate (0.34 g, 2 mmol) in DMSO (10 mL) was stirred at rt for 30 min under N2. Then to the reaction mixture was added a solution of 5-methylpyridone (1.09 g, 10 mmol) and 4-(2-fluoro-4-iodobenzyl) morpholine (3.21 g, 10 mmol) in DMSO (12 mL) via syringe. The reaction mixture was heated at 100 C. overnight, cooled to rt and filtered. The filtrate diluted with H2O (50 mL) was extracted with CH2Cl2 (50 mL*3). The combined organic phases were concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=10:1) to give the title compound as a white solid (0.70 g, 23%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 303.2 (M+1); 1H-NMR (400 MHz, CDCl3): delta 2.06 (s, 3H), 3.16-3.32 (m, 4H), 3.86-3.97 (m, 4H), 4.44 (s, 2H), 6.47 (d, 1H, J=9.6 Hz), 7.39-7.44 (m, 2H), 7.48 (s, 1H), 7.52-7.55 (m, 1H), 7.99 (t, 1H, J=8.2 Hz).

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, 1003-68-5, 5-Methylpyridin-2(1H)-one.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; Zhang, Yingjun; Zhang, Jiancun; Wang, Xiaojun; Lin, Runfeng; Cao, Shengtian; Wang, Zhaohe; Li, Jing; US2015/87639; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 1003-68-5, name is 5-Methylpyridin-2(1H)-one. This compound has unique chemical properties. The synthetic route is as follows. 1003-68-5

1 (10.9 g, 0.1 mol) and 2 (31.6 g, 0.12 mol) were dissolved in dry DMF (200 mL) under N2 atmosphere, then anhydrous K2CO3 (27.6 g, 0.2 mol) and CuI (3.8 g, 0.02 mol) were added. The reaction mixture was refluxed for 10 h. After cooling, the mixture was quenched with saturated NaHCO3 (aq, 150 mL), and extracted with EtOAc (3¡Á50 mL), the organic layers were collected, dried over anhydrous Na2SO4, filtered and concentrated, crystallized from EtOAc /PE. The desired product 3 was obtained as a yellowish solid (21.5 g, 74%), mp: 123-124. 1HNMR (400MHz, CDCl3): delta 7.05-7.46 (m, 11H), 6.62 (d, J=9.2 Hz, 1H), 5.11 (s, 2H), 2.10 (s, 3H).

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, 1003-68-5, 5-Methylpyridin-2(1H)-one.

Reference:
Article; Ma, Zhen; Pan, Youlu; Huang, Wenhai; Yang, Yewei; Wang, Zunyuan; Li, Qin; Zhao, Yin; Zhang, Xinyue; Shen, Zhengrong; Bioorganic and Medicinal Chemistry Letters; vol. 24; 1; (2014); p. 220 – 223;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

1003-68-5, 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. 1003-68-5, name is 5-Methylpyridin-2(1H)-one. This compound has unique chemical properties. The synthetic route is as follows.

To a 25 mL round bottom flask was added 0.10 g (1 mmol, 1 quiv.) Of compound 3,0.17 g (1 mmol, 1 quiv.) Bromobenzene, 1.4 g (10 mmol, 10 equiv.) K2CO3,0.05 g (0.26 mmol, 0.25 equiv.) CuI,5 mL of DMF as solvent,Reflux stirring reaction 1h,TLC followed by reaction completion, cooling, adding 30 mL of water, 3 x 20 mL of ethyl acetate extraction, and an organic layer of anhydrous sulfuric acidSodium dry, spin dry, 300 mesh silica gel column chromatography, eluent petroleum ether: ethyl acetate = 1: 3 (v / v) to give pirfenidone,The yield was 76%.

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, 1003-68-5, 5-Methylpyridin-2(1H)-one.

Reference:
Patent; Sichuan Univeristy; Yi, Shufan; Li, Yong; Cao, Tingting; Yang, Ziyao; (17 pag.)CN106083702; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 1003-68-5 as follows., 1003-68-5

To 144 5-methyl-1H-pyridin-2-one (2.0 g, 18 mmol), 96 1-iodo-4-(trifluoromethyl)benzene (5.9 g, 22 mmol), 12 copper(I) iodide (6.7 g, 3.6 mmol), 13 potassium phosphate (7.7 g, 37 mmol) and 145 N,N’-dimethylethylenediamine (0.70 g, 7.3 mmol) was added 126 1,4-dioxane (15 mL), and the mixture was stirred under a nitrogen atmosphere at 109C overnight. Insoluble material was filtered off through celite, the filtrate was poured into water and the mixture was extracted three times with ethyl acetate. The organic layer was dried over sodium sulfate. The desiccant was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate) to give the 146 title compound (4.2 g, 17 mmol, 91%). 1H NMR (400 MHz, DMSO-d6) delta7.90 (d, J = 8.0 Hz, 2H), 7.68 (d, J = 8.4, Hz, 2H), 7.52 (s, 1H) 7.41 (dd, J = 2.8, 9.6 Hz, 1H), 6.48 (d, J = 9.2 Hz, 1H) 2.05 (s, 3H).

The chemical industry reduces the impact on the environment during synthesis 1003-68-5, I believe this compound will play a more active role in future production and life.

Reference:
Patent; EA Pharma Co., Ltd.; KOBAYASHI, Kaori; SUZUKI, Tamotsu; OKUZUMI, Tatsuya; (110 pag.)EP3412664; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

1003-68-5, 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. 1003-68-5, name is 5-Methylpyridin-2(1H)-one. This compound has unique chemical properties. The synthetic route is as follows.

Add the product of the previous step (6.87mmol) to DMF,5-methylpyridone (4.58 mmol), anhydrous potassium carbonate (5.50 mmol) and CuI (0.55 mmol), the mixture was heated to 140 C for 5 hours, cooled to room temperature.After filtration, the filtrate was collected, and the DMF was evaporated to dryness, then ethyl acetate was dissolved, washed with water and brine, and then dried and evaporated.A white solid was obtained which was used directly in the next step.

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, 1003-68-5, 5-Methylpyridin-2(1H)-one.

Reference:
Patent; Hangzhou He Zheng Pharmaceutical Co., Ltd.; Zhou Xinglu; Liu Xingguo; Hu Miao; Dong Xiaowu; Huang Wenhai; (62 pag.)CN109535200; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

1003-68-5, Adding a certain compound to certain chemical reactions, such as: 1003-68-5, 5-Methylpyridin-2(1H)-one, 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, 1003-68-5, blongs to pyridine-derivatives compound.

A single-necked flask was charged with 0.1 g (1 mmol) of 5-methyl-2 (1H)one 0.14 g K2CO3, 0.17 g p-bromobenzaldehyde,0.05 g CuI, 5 ml DMF as solvent,The reflux reaction was carried out,TCL monitoring to the reaction is completed,Stop reaction, filter,The filtrate was extracted with EA (ethyl acetate)The organic layer was concentrated (PE: EA = 3: 1, volume ratio, PE was petroleum ether)To give a yellowish or white flake solid 0.08 g,That is compound 1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1003-68-5, its application will become more common.

Reference:
Patent; Sichuan University; Yin, Shufan; Li, Yong; Cao, Tingting; Yuan, Li; Song, Zhangwei; (16 pag.)CN106397408; (2017); A;,
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. 1003-68-5, name is 5-Methylpyridin-2(1H)-one. A new synthetic method of this compound is introduced below., 1003-68-5

A mixture of 5 -methyl- lH-pyridin-2-one (100 g), bromo benzene (259 g, comprising greater than 0.2% by weight dibromobenzene isomers) and dimethylformamide (200 ml) were added in to a round bottom flask and stirred up to complete dissolution. Potassium carbonate (254 g) and copper (I) chloride (18.2 g) was added to the above reaction mass and then heated to 130-140C. The reaction mass was stirred at 130-140C for 10 hrs. After the reaction completion, the reaction mass was cooled to 25-35C. Toluene (500 ml), aqueous sodium chloride (75 g of sodium chloride in 500 ml of water) was added to the reaction mass and stirred for 15-30 mins at 25-35C. The reaction mass was filtered and the filtrate was allowed to settle. Organic and aqueous layers were separated and the aqueous layer was extracted with toluene. Organic layers combined and was washed with aqueous sodium chloride, treated with carbon and filtered through hyflo. The solvent from the filtrate was distilled off completely under vacuum at below 60C. Toluene (300 ml) was added to the obtained residue and stirred for 30 mins. The reaction mass was heated to 77-83C and stirred for 45 mins. The reaction mass was cooled to 25-35C over 60 mins. The reaction mass was further cooled to 0-6C. The solid obtained was filtered, washed with toluene and dried under vacuum. DM water (500 ml) was added to the above obtained wet compound followed by 50% aqueous sodium hydroxide solution (10 g of sodium hydroxide in 20 ml of water) at 25-35C. The reaction mass was heated to 75-85C and stirred for 30-60 mins. The reaction mass was then gradually cooled to 25-35C and stirred for 60 mins. The reaction mass was further cooled to 0-5 C and stirred for 3 hrs. The obtained solid was filtered, washed with water and dried to provide the title compound.Yield: 120 g; purity by HPLC: 99%; The XRPD is set forth in Figure 1 The DSC is set forth in Figure 2.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1003-68-5, 5-Methylpyridin-2(1H)-one, and friends who are interested can also refer to it.

Reference:
Patent; LAURUS LABS LIMITED; BOLLU, Ravindra Babu; MANDADAPU, Venkata Pramod Kumar; INDUKURI, Venkata Sunil Kumar; CHAVA, Satyanarayana; (20 pag.)WO2017/122139; (2017); 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. 1003-68-5, name is 5-Methylpyridin-2(1H)-one. A new synthetic method of this compound is introduced below., 1003-68-5

EXAMPLE 4 5-Methyl-1-p-tolyl-2-(1H)-pyridone The reaction of p-iodotoluene with 5-methyl-2-(1H)-pyridone by the reaction of Example 1, affords 5-Methyl-1-p-tolyl-2-(1H)-pyridone in 89% yield.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1003-68-5, 5-Methylpyridin-2(1H)-one, and friends who are interested can also refer to it.

Reference:
Patent; Affiliated Medical Research, Inc.; US3974281; (1976); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem