Month: November 2020

25597-16-4, A common heterocyclic compound, 25597-16-4, name is Ethyl 4,4,4-trifluorocrotonate, molecular formula is C6H7F3O2, 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.

The resulting product (0.45g, 1.9mmol) from step 4, ethyl 4,4,4-trifluorocrotonate (1.3g, 7.6mmol) and anhydrous potassium carbonate (2.6g, 1.9mmol) were dissolved in DMF (10mL), and then the system was stirred for 2hrs at 90C. At the end of reaction, the reaction system was cooled to room temperature and added with water, the mixture was extracted with ethyl acetate, and the organic phase was dried and evaporated in vacuum to obtain 0.40g of the product (55%) by column chromatography. 1HNMR (400 MHz, d-CDCl3), delta 7.88(s, 1H), 6.76 (s, 1H), 5.7(m, 1H), 4.3(dd, 2H),1.35(t, 3H) MS (MM-ES+APCI), m/z: 384 (M-H+)

The synthetic route of 25597-16-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangzhou Institute Of Biomedicine And Health, Chinese Academy Of Sciences; ZHANG, Yanmei; TALLEY, John Jeffrey; OBUKOWICZ, Mark G.; TU, Zhengchao; TORTORELLA, Micky; WANG, Yican; LIU, Jianqi; CHEN, Yan; LIU, Xiaorong; LU, Xin; EP2845854; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 24398-88-7, name is Ethyl 3-bromobenzoate, 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. 24398-88-7

General procedure: To an undivided electrochemical cell, fitted with an iron/nickel (64/36) rod as the anode and surroundedby a nickel foam as the cathode, were added DMF (50 mL), tetrabutylammonium bromide (1.2 mmol, 400mg), and 1,2-dibromoethane (2.5 mmol, 215 muL). The mixture was electrolyzed under argon at a constantcurrent intensity of 0.2 A at room temperature for 15 min. The current was then stopped, and the NiBr2bpycomplex (0.4 mmol, 150 mg), 3-amino- or 3-alkoxy/aryloxy-6-chloropyridazine (4 mmol), and aromatic orheteroaromatic halides (8 mmol) were sequentially added. The solution was electrolyzed at 0.2 A at roomtemperature until one of the starting materials was totally consumed. A saturated aqueous solution of EDTAsodium salt (100 mL) was added to the mixture, and the solution was extracted with dichloromethanecontaining 2-5% methanol (3 ¡Á 100 mL). The combined organic layers were dried over MgSO4, filtered,and evaporated under vacuum. The crude product was purified by flash chromatography on silica, elutedwith a gradient of solvents (pentane/acetone). For some polar cross-coupling compounds, a mixture ofacetone/methanol (95/5) was necessary.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 24398-88-7.

Reference:
Article; Sengmany, Stephane; Sitter, Mathilde; Leonel, Eric; Le Gall, Erwan; Loirand, Gervaise; Martens, Thierry; Dubreuil, Didier; Dilasser, Florian; Rousselle, Morgane; Sauzeau, Vincent; Lebreton, Jacques; Pipelier, Muriel; Le Guevel, Remy; Bioorganic and Medicinal Chemistry Letters; vol. 29; 5; (2019); p. 755 – 760;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

24398-88-7, A common heterocyclic compound, 24398-88-7, name is Ethyl 3-bromobenzoate, molecular formula is C9H9BrO2, 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.

1-(6-(dibutyl(3-(ethoxycarbonyl)phenyl)stannyl)hexyl)-3-ethyl-1H-imidazol-3-ium bromide I’a-14(Br-) A dried 50 mL Schlenk tube was flushed with argon and charged with zinc dust (1.36 g, 20.8 mmol, 5 eq) and cobalt(II) bromide (0.095 g, 0.4190.434 mmol, 0.1 eq). The mixture was activated under vacuum at 150C during 4 h. Acetonitrile (5 mL) was added to the cooled mixture then trifluoroacetic acid (0.15 mL) and 1,2-dibromoethane (0.1 mL) were added and the resulting solution stirred for additional 15 minutes (an increase of temperature was observed). Then ethyl 3-bromobenzoate (1.46 g, 6.36 mmol, 6.3 eq) was introduced to the mixture which was stirred at room temperature for 12 h. The resulting solution of arylzinc reagent was introduced dropwise to the ionic liquid (Va-1) (529 mg, 1.0 mmol, 1 eq) in solution in THF (6 mL). After 18 h of stirring at room temperature, the resulting mixture was filtered through a short pad of silica gel then extracted with CH2Cl2 (3 x 100 mL). The combined organic layers were dried over MgSO4 and concentrated under reduced pressure. The crude product was purified by silica gel chromatography (CH2Cl2 to CH2Cl2/MeOH 90:10) to afford compound I’a-14(Br-) as viscous yellow oil (450 mg, 70 %). 1H NMR (CDCl3): delta 10.17 (s, 1H), 8.14 (bs, 1H), 7.92 (d, J = 7.8 Hz, 1H), 7.62 (d, J = 7.2 Hz, 1H), 7.39 (dd, J = 7.5 Hz, J = 7.5 Hz, 1H), 7.30 (bs, 1H), 7.23 (bs, 1H), 4.48-4.33 (m, 4H), 4.32 (t, 2H, J = 7.2 Hz), 1.89-1.78 (m, 2H), 1.61-1.47 (m, 9H), 1.42-1.24 (m, 11H), 1.13-1.00 (m, 6H), 0.87 (t, J = 7.2 Hz, 6H). 13C NMR 75 MHz (CDCl3) delta (ppm): 166.8, 141.9, 140.6, 136.9, 135.9, 129.4, 128.8, 127.5, 122.0, 121.8, 60.6, 49.8, 45.1, 33.4, 30.0, 28.7, 27.0, 26.3, 25.5, 15.5, 14.4, 13.4, 9.4, 9.3. HRMS (FAB) calcd. for C28H47N2O2Sn 563.2654 [M-Br]+; found 563.2675.

The synthetic route of 24398-88-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Centre National de la Recherche Scientifique (CNRS); UNIVERSITE DE NANTES; UNIVERSITE D’ANGERS; Universite du Maine; Institut National de la Sante et de la Recherche Medicale (INSERM); Centre Hospitalier Universitaire De Nantes; Legoupy, Stephanie; Faye, Djibril; Gestin, Jean-Francois; Rajerison, Holisoa; Faivre-Chauvet, Alain; Boeda, Fabien; EP2891657; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

25597-16-4, A common compound: 25597-16-4, name is Ethyl 4,4,4-trifluorocrotonate, belongs to esters-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

Step 6: ethyl 8-chloro-6-(methyl-D3)-2-(trifluoromethyl)-2H-chromene-3-carboxylate The resulting product (0.25 g, 1.4 mmol) from step 5, ethyl 4,4,4-trifluorocrotonate (0.48 g, 2.8 mmol) and anhydrous potassium carbonate (0.46 g, 2.8 mmol) were dissolved in DMF (10 mL), and then the system was stirred for 3 hrs at 90 C. At the end of reaction, the reaction system was cooled to room temperature and added with water, the mixture was extracted with ethyl acetate, and the organic phase was dried and evaporated in vacuum to obtain 0.2 g of the product (44%) by column chromatography. 1HNMR (400 MHz, d6-DMSO), delta 7.39 (s, 1H), 7.31 (s, 1H), 6.1 (m, 1H), 4.27 (dd, 2H), 1.30 (t, 3H) MS (MM-ES+APCI), m/z: 325 (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, Ethyl 4,4,4-trifluorocrotonate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences; Zhang, Yanmei; Talley, John Jeffrey; Obukowicz, Mark G.; Tu, Zhengchao; Tortorella, Micky; Wang, Yican; Liu, Jianqi; Chen, Yan; Liu, Xiaorong; Lu, Xin; US2015/133538; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 1865-29-8, name is Methyl 2-phenylacrylate, molecular formula is C10H10O2, 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. 1865-29-8

PREPARATION 21 Methyl (RS)-4-cyano-2-Phenylbutanoate STR75 Lithium diisopropylamide (3.67 ml of a 1.5 molar solution in cyclohexane) was added to acetonitrile (0.26 ml) in tetrahydrofuran (10 ml) at -78 C. After 1 hour, methyl 2-phenyl-acrylate (see Preparation 22) (0.81 g) in tetrahydrofurn (10 ml) was added and the mixture was stirred for 1 hour, allowed to warm to room temperature then treated with saturated ammonium chloride solution. The resulting mixture was partitioned between ethyl acetate and water, the organic phase dried over magnesium sulphate and evaporated to give a residue which was partitioned between ether and 10% aqueous sodium carbonate. The organic layer was dried over magnesium sulphate and evaporated to leave the title compound (0.5 g, 75%) as an oil. 1 H-NMR (300 MHz, CDCl3), delta=2.0-2.4 (m, 4H), 3.7 (s, 3H), 3.8 (t, 1H), 7.2-7.5 (m, 5H) ppm. I.R. (thin film) 2220 cm-1 (C=N).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1865-29-8, its application will become more common.

Reference:
Patent; Pfizer Inc.; US5292749; (1994); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 37746-78-4, name is (E)-Ethyl 4-bromobut-2-enoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 37746-78-4

The compound of formula 7-4 (3.0 g, 8.7 mmol, 1 eq) was dissolved in acetonitrile,Ethyl bromocrotonate (1.86 g, 9.6 mmol, 1.1 eq) and potassium carbonate (2.42 g, 17.5 mmol, 2 eq) were added. After the addition, the temperature was raised to 85 C. and the reaction was continued overnight.After the completion of the reaction by thin layer chromatography, the mixture was filtered and spin-dried. Ethyl acetate and water were dissolved and diluted. The layers were separated, and the aqueous phase was extracted with ethyl acetate. The organic phase was combined.After washing with saturated saline, it was dried over anhydrous sodium sulfate, filtered, and spin-dried to obtain 3.94 g of a brown oil (compound of formula 7-5) in 98% yield.

The synthetic route of 37746-78-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Yangfan Pharmaceutical Technology Co., Ltd.; Chen Youxi; Gao Fei; He Lidong; (80 pag.)CN104109143; (2018); B;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

A common heterocyclic compound, 154825-97-5, name is Methyl 2-(4-bromophenyl)-2,2-dimethylacetate, molecular formula is C11H13BrO2, 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. 154825-97-5.

EXAMPLE 12; 4 -R (1S)-1-[[(1S)-1-[[(1-cyanocyclopropyl)amino]carbonyl]-3-fluoro-3-methylbutyl]amino]-2,2,2- TRIFLUOROETHYLL-A, CT-DIMETHYL- (1, 1 -BI HENVLL-4-ACETIC acid; STEP 1 : 2- (4-BROMOPHENYL)-2-METHYLPROPANOIC acid; To a 0 C solution of diisopropylamine (1.52 mL) in THF (50 mL) was slowly added butyllithium (4.3 mL). The reaction mixture was stirred at 0 C for 15 minutes. It was cooled to-78 C and a solution of methyl 2- (4-bromophenyl) propanoate from Example 11 Step 2 (2.4 g) in THF (25 ML) was slowly added. The mixture was stirred at-78 C for 30 minutes. Then a solution of iodomethane (2.5 mL) in THF (25 mL) was added dropwise and the mixture was stirred at-78 C for 30 minutes then warmed up slowly to room temperature and stirred for 1 HOUR. H NMR showed 50% conversion. The reaction mixture was cooled to 0 C and 20 mL of potassium t-butoxid (1.0 M in THF) was added dropwise. The mixture was stirred at 0 C for 30 minutes, warmed up to room temperature and stirred for 1 hour. The reaction mixture was poured into ice (50 g) and saturated aqueous ammonium chloride (100 mL), extracted with ethyl acetate (3 x 100 mL). The combined extracts were washed with brine, dried with magnesium sulfate and the solvent removed in vacuo to yield a residue which was diluted with THF (30 ML) and methyl alcohol (15 mL). The solution was cooled to 0 C and 20 mL of lithium hydroxide (1.0 N) was added. The mixture was stirred at room temperature for 3 hours. Then the reaction mixture was poured into ice and 1N HC1 and extracted with dichloromethane (2 x 100 mL). The combined extracts were washed with brine, dried with magnesium sulfate and the solvent removed in vacuo. The residue was purified by swish using diethyl ether and hexanes to yield the title compound. ‘H NMR (CD3COCD3) 8 10.85 (1H, bs), 7.53 (2H, d), 7.48 (2H, d), 1.50 (6H, s).

The synthetic route of Methyl 2-(4-bromophenyl)-2,2-dimethylacetate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK FROSST CANADA & CO.; WO2005/19161; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 609-12-1, name is Ethyl 2-bromo-3-methylbutanoate, 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. 609-12-1

A) ethyl 2-(3-cyano-4-methoxy-2-oxopyridin-1(2H)-yl)-3-methylbutanoate (0774) A mixture of 4-methoxy-2-oxo-1,2-dihydropyridine-3-carbonitrile (5.0 g), ethyl 2-bromo-3-methylbutanoate (10.4 g), cesium carbonate (32.6 g) and N,N-dimethylformamide (75 mL) was stirred at 50C overnight. The reaction mixture was added to water, and the mixture was extracted twice with ethyl acetate. The extracts were combined, washed with water and then saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (6.11 g). MS (ESI+): [M+H]+ 279.2.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 609-12-1.

Reference:
Patent; Takeda Pharmaceutical Company Limited; YOSHIDA, Masato; NAGAMIYA, Hiroyuki; OHBA, Yusuke; SETO, Masaki; YOGO, Takatoshi; SASAKI, Satoshi; TOKUNAGA, Norihito; ASO, Kazuyoshi; (298 pag.)EP2980089; (2016); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

33993-24-7, The chemical industry reduces the impact on the environment during synthesis 33993-24-7, name is Cyclopropanecarboxylic anhydride, I believe this compound will play a more active role in future production and life.

To a suspension of Compound Int-28d (0.51 g, 1.87 mmol) in CH2C12 (3 mL) was added cyclopropyl anhydride (2 mL). The resulting reaction was allowed to stir at room temperature for 2 hours, then a solution of 4M HC1 in dioxane ( 3 mL) was added and the reaction was allowed to stir at room temperature for 2 hours. The reaction mixture was then filtered and the collected solid was washed with hexane and dried under vacuum to provide Compound Int-29a (590 mg). MS (ESI) m / e (M+H+): 323.

The chemical industry reduces the impact on the environment during synthesis Cyclopropanecarboxylic anhydride. I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KOZLOWSKI, Joseph, A; ROSENBLUM, Stuart, B; COBURN, Craig, A; SHANKAR, Bandarpalle, B; ANILKUMAR, G, Nair; CHEN, Lei; DWYER, Michael, P; JIANG, Yueheng; KEERTIKAR, Kartik, M; LAVEY, Brian, J; SELYUTIN, Oleg, B; TONG, Ling; WONG, Michael; YANG, De-Yi; YU, Wensheng; ZHOU, Guowei; WU, Hao; HU, Bin; ZHONG, Bin; SUN, Fei; JI, Tao; SHEN, Changmao; WO2012/40923; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 3196-15-4, name is Methyl 2-bromobutyrate, 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 3196-15-4. 3196-15-4

[1014] Step 3: methyl 3-(1-methoxy-1-oxobutan-2-yl)-2-(4-methylbenzoylimino)-2,3-dihydrobenzo[d]thiazol-6-carboxylate[1015] To the mixture of methyl 2-(4-methylbenzamido)benzo[d]thiazol-6-carboxylate and 2-(4-methylbenzamido)benzo[d]thiazol-6-carboxylic acid (100 mg, 0.32 mmol) prepared in Step 2 in dimethylformamide (1.5 mL) were added potassium carbonate (133 mg, 0.96 mmol) and methyl 2-bromobutyrate (55 uL, 0.48 mmol). The reaction mixture was refluxed under stirring at 80 ? overnight. The reaction mixture was quenched with water and then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered, and then evaporated. The residue was purified with preparative thin layer chromatography (n-hexane/ethyl acetate = 4/1) to give 50 mg of the titled compound as a white solid (Yield: 37%).[1016] 1H NMR (DMSO-d 6 , 400 MHz) delta 8.61(s, 1H), 8.12(d, 1H), 8.06(d, 2H), 7.93(d, 1H), 7.34(d, 2H), 5.90(m, 1H), 3.90(s, 3H), 3.59(s, 3H), 2.40-2.50(m, 5H), 0.77(t, 3H)

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of Methyl 2-bromobutyrate.

Reference:
Patent; YUHAN CORPORATION; HUR, Youn; KIM, Dong-Hyun; KIM, Eun-Kyung; PARK, Jin-Hwi; JOO, Jae-Eun; KANG, Ho-Woong; OH, Se-Woong; KIM, Dong-Kyun; AHN, Kyoung-Kyu; WO2013/43001; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics