Month: March 2021

Adding a certain compound to certain chemical reactions, such as: 106614-28-2, name is Methyl 2,4-difluorobenzoate, belongs to esters-buliding-blocks compound, 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 106614-28-2, Product Details of 106614-28-2

To a solution of methyl 2, 4-difluorobenzoate (3.44 g, 20.00 mmol) in DMF (50 mL) was added 1H-pyrrolo [2, 3-b] pyridin-5-ol (2.70 g, 20.00 mmol) and K 2CO 3 (5.6 g, 40.00 mmol), the mixture was stirred at 80C for 20h. Cooled to room temperature, partitioned between EA (40 ml) and H 2O (40 mL), the aqueous layer was extracted with EA (20 mL). The combined organic layers were washed with H 2O (30 mL3), concentrated and purified by CombiFlash (0-60%, EA/PE) to give the crude product, which was crystallized from EA/PE=1/1 (50 mL) to give the isomer. The mother liquid was left standing over night, the precipitate was collected by filtration to give methyl 2- ((1H-pyrrolo [2, 3-b] pyridin-5-yl) oxy) -4-fluorobenzoate (600 mg) as a white solid. [M+1] + 286.9.

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, Methyl 2,4-difluorobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BEIGENE, LTD.; GUO, Yunhang; XUE, Hai; WANG, Zhiwei; SUN, Hanzi; (493 pag.)WO2019/210828; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 37746-78-4,Some common heterocyclic compound, 37746-78-4, name is (E)-Ethyl 4-bromobut-2-enoate, molecular formula is C6H9BrO2, 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.

General procedure: A mixture of 1-(1H-pyrrol-2-yl) ethanone 1 (109 mg, 1.0 mmol), (E)-ethyl 4-bromobut-2-enoate 2 (256 mg, 1.0 mmol), and K2CO3 (414 mg, 3.0 mmol) in CH3CN (5 mL)was refluxed. The end of the reaction was monitored by the TLC. Ice water(100 mL) was poured into the mixture and CH2Cl2 (3 30 mL) was used toextract the mixture. The combined organic layers were dried over Na2SO4,filtered, and concentrated in vacuo. Purification by flash columnchromatography (Hexane/EtOAc = 10:1, v/v) afforded the desired product 7

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

Reference:
Article; Yang, Bingchuan; Huang, Zixiao; Guan, Hegen; Niu, Xiaoyi; Li, Yanqiu; Fang, Shuai; Ma, Chen; Tetrahedron Letters; vol. 54; 45; (2013); p. 5994 – 5997;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 89-91-8, 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. 89-91-8, name is Methyl 2,2-dimethoxyacetate, This compound has unique chemical properties. The synthetic route is as follows.

Intermediate 55a: heptyl 2,2-bis(heptyloxy)acetate To a solution of methyl 2,2-dimethoxyacetate (5.0g, 37.3 mmol) in heptanol (26.3 ml_, 186 mmol) was added camphorsulfonic acid (0.43g, 1.86 mmol), and the reaction was heated to 100 C, overnight. The reaction was cooled to ambient temperature and concentrated under reduced pressure. The concentrate was purified on silica gel with dichloromethane / heptane as eluent to provide 4.0g of the desired compound. 1H NMR (400 MHz, CDCI3): delta = 4.86 (s, 1 H), 4.21 (t, J = 6.78 Hz, 2H), 3.52-3.69 (m, 4H), 1.55-1.77 (m, 6H), 1.20-1.45 (m, 24H), 0.82- 0.98 (m, 9H) ppm.

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

Reference:
Patent; NOVARTIS AG; BRITO, Luis; CHEN, Delai; GAMBER, Gabriel Grant; GEALL, Andrew; LOVE, Kevin; ZABAWA, Thomas; ZECRI, Frederic; WO2015/95346; (2015); A1;,
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. 20330-90-9, name is Dimethyl 5-chloroisophthalate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of Dimethyl 5-chloroisophthalate

To a solution of 1,3-dimethyl 5-chlorobenzene-l ,3-dicarboxylate (4.00 g, 17.5 mmol) in dioxane (50 mL) and water (50 mL) was added NaOH (700 mg, 17.5 mmol). The resulting suspension was stirred vigorously at 40C for 2 hrs and then for a further 16 hrs at room temperature. The reaction mixture was evaporated to dryness, re-dissolved in water (-200 mL) and acidified to pH 3 using 1M HCl. The resulting white precipitate was sonicated for 2 mins and filtered. The white solid was washed further with water and then dried in a vacuum oven overnight. This afforded a white solid (3.6 g) which was a mixture of 3 products including 3-chloro-5-(methoxycarbonyl)benzoic acid. This solid was dissolved in DMF (150 mL) at 0C and diethylamine (2.56 g, 0.03 mol), DIPEA (6.09 ml, 0.03 mol) and HATU (6.64 g, 0.02 mol) were added. The reaction mixture was then stirred at room temperature for 6 hrs then evaporated to dryness, re- dissolved in EtOAc (200 mL) and washed with water (3 x 200 mL) and brine (2 X200 mL). The combined organics were then dried over MgSC>4 and evaporated to dryness to afford the crude product. This was purified by silica chromatography (Biotage: lOOg SNAP cartridge) eluting with 0-80% EtOAc in heptane to afford the title compound as a colourless oil (880 mg (28%); H NMR (500 MHz, CDC13) 5 1.13 (br. s, 3H), 1.26 (t, 3H), 3.24 (br.s, 2H), 3.54 (br. s, 2H), 3.93 (s, 3H),7.55 (m, 1H), 7.92 (m, 1H), 8.04 (m, 1H).

The synthetic route of 20330-90-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACTIVE BIOTECH AB; FRITZSON, Ingela; LIBERG, David; EAST, Stephen; MACKINNON, Colin; PREVOST, Natacha; WO2014/184234; (2014); A1;,
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. 2051-59-4, name is 6-Chloro-2H-chromen-2-one belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 6-Chloro-2H-chromen-2-one

General procedure: A flame-dried reaction vessel with a magnetic stirring bar was sequentially charged with coumarin or p-dimethoxybenzene or 7-(2-Chloroethyl)theophylline (0.4mmol), PC (0.004mmol), pyridine N-oxide (0.82mmol, 78mg), CH2Cl2 (0.5mL) and CH3CN (0.5mL). Trifluoroacetic anhydride (0.8mmol, 168mg) was then added to the resulting homogeneous solution. The mixture was stirred at room temperature under irradiation from a blue LED. The solvent in the reaction mixture was removed under reduced pressure. The residue was redissolved in 2mL of CH3CN, and extracted 5 times with hexane (5mL each time). The PC was extracted into the hexane layer and separated for use in the next reaction. The CH3CN layer was dried with Na2SO4 and concentrated under vacuum. After separation and evaporation, the residue was purified by column chromatography on silica gel (200-300 mesh size) using petroleum ether/EtOAc as the eluent to give the trifluoromethyl coumarin.

The synthetic route of 2051-59-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Xiaodan; Li, Yaming; Hao, Xinyu; Jin, Kun; Zhang, Rong; Duan, Chunying; Tetrahedron; vol. 74; 15; (2018); p. 1742 – 1748;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 91085-56-2, name is Ethyl 3,5-dichlorobenzoate, A new synthetic method of this compound is introduced below., name: Ethyl 3,5-dichlorobenzoate

5,6-Dihydro-cyclopenta[b]thiophen-4-one (2.1 g, 15.0 mmol) in 15 ml of THF was treated with NaH (60 percent, 1.5 g, 36 mmol). After the addition of 3,5-Dichloro-benzoic acid ethyl ester, the reaction mixture was heated at 100 C. for 8 hr. The solution was cooled to room temperature and poured into water. The resulting mixture was acidified with concentrated HCl and was added with ethyl acetate (70 mL). The organic layer was collected, brined, dried over MgSO4(s), and concentrated under reduced pressure. The resultant precipitate was collected and recrystallized from ethanol to provide the corresponding 5-(3,5-Dichloro-benzoyl)-5,6-dihydro-cyclopenta[b]thiophen-4-one (1.5 g, 4.8 mmol) as brown solid in 34% yield.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; DEVELOPMENT CENTER FOR BIOTECHNOLOGY; LIAO, Chu-Bin; CHIANG, Chao-Cheng; YANG, Huei-Ru; LIAO, Yuan-Chun; CHEN, Paonien; US2013/274255; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 116419-94-4, name is Methyl 4-methyl-3-(trifluoromethyl)benzoate, This compound has unique chemical properties. The synthetic route is as follows., category: esters-buliding-blocks

To a solution of methyl-4-methyl-3-(trifluoromethyl) benzoate (1 equiv) in chloroform was added N-bromosuccinimide (1.1 equiv) and benzoyl peroxide (0.01 equiv). The reaction mixture was heated at reflux overnight (18h). It was then cooled to room temperature, washed with water, dried over Na2S0 and concentrated. It was purified by silica gel chromatography (eluted with 1% ethyl acetate/hexane) to provide the title compound (65% yield). ESI MS m/z -297.

According to the analysis of related databases, 116419-94-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NATCO PHARMA LIMITED; KOMPELLA, Amala; GAMPA, Venugopala Krishna; GANGANAMONI, Srinivasulu; SIRIGIREDDY, Balakrishna Reddy; ADIBHATLA, Kali Satya Bhujanga Rao; NANNAPANENI, Venkaiah Chowdary; WO2015/186137; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 46064-79-3, A common heterocyclic compound, 46064-79-3, name is Methyl 3-amino-4-bromobenzoate, molecular formula is C8H8BrNO2, 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 intermediate compound prepared in step 4 (100 mg, 0.26 mmol) to N, N-dimethylformamide (2.6 ml) was addedAnd methyl 3-amino-4-bromobenzoate (59.8 mg, 0.26 mmol)And bis (triphenylphosphine) palladium (II) dichloride (21 mg, 0.03 mmol),Copper (I) iodide (5.7 mg, 0.03 mmol),Triethylamine (0.1 ml, 0.8 mmol) was added thereto, followed by stirring at 80 C for 4 hours.The reaction mixture was diluted with ethyl acetate and washed with distilled water.Dried over magnesium sulfate, filtered, concentrated and purified by silica gel chromatography to obtain the intermediate compound methyl 3-Amino-4 – ((2-chloro-4 – ((5- cyclopropyl-3- (2,6-dichlorophenyl)Isoxazol-4-yl) methoxy)Phenyl) ethynyl) benzoate (98.9 mg, 67%).

The synthetic route of 46064-79-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ildong Pharmaceutical Co., Ltd.; Kang Jae-hun; Lee Hong-seop; Lee Yun-seok; Jeong Jin-a; Kwon Seong-uk; Kim Gyeong-seon; Song Dong-geun; Choi Ji-hye; Hwang Hye-min; (43 pag.)KR2018/115126; (2018); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 816-27-3, 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. 816-27-3, name is Ethyl 2-ethoxy-2-iminoacetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A mixture of 4-chloropyridine-3-sulfonamide (500 mg, 2.6 mmol), ethyl 2-ethoxy-2- iminoacetate (565 mg, 3.9 mmol) and DBU (790 mg, 5.2 mmol) in ethanol (10 mL) was heated in a sealed tube at 150 C for 0.5 h then cooled to r.t.. The mixture was diluted with water (5 mL), adjusted to pH 5 with 1 M aqueous HCI and exacted with DCM (10 mL x 3). The combined organic extracts were washed with brine, dried over sodium sulfate and concentrated. The residue was purified by preparative TLC (MeOH/DCM = 1 :20, v/v) to give the product as a yellow solid (100 mg, 15% yield). LCMS (ES-API) Rt 0.47 min; m/z 256 [M+H]+. 1H NMR (400 MHz, d6-DMSO), 9.05 (s, 1H), 8.76 (d, J = 5.6 Hz, 1H), 7.64 (d, J = 5.6 Hz, 1H), 4.40 (q, J = 7.2 Hz, 2H), 1.37 (t, J = 7.2 Hz, 3H).

The synthetic route of Ethyl 2-ethoxy-2-iminoacetate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CTXT PTY LIMITED; MORROW, Benjamin Joseph; FOITZIK, Richard Charles; CAMERINO, Michelle Ang; LAGIAKOS, Helen Rachel; WALKER, Scott Raymond; BOZIKIS, Ylva Elisabet Bergman; STEVENSON, Graeme Irvine; CUZZUPE, Anthony Nicholas; STUPPLE, Paul Anthony; (313 pag.)WO2019/43139; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 27798-60-3, 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. 27798-60-3 name is Methyl 2-Methoxyphenylacetate, This 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.

Methyl bromo-(2-methoxyphenyl)acetate; A mixture of 14.6 g (81.2 mmol) of methyl (2-methoxyphenyl)acetate, 15.2 g (85.3 mmol) of Lambda/-bromosuccinimide and a catalytic amount of AIBN in tetrachloromethane (180 ml) was heated under reflux with stirring for 2h. The cooled reaction solution was filtered, and the solvent was removed in vacuo. Yield: 21.6 g (100%) of yellow oil 1H-NMR (CDCI3): 3.78 (s, 3H), 3.87 (s, 3H), 5.90 (s, 1 H), 6.88 (d, 8.31 Hz, 1 H), 6.99 (t, 7.5 Hz, 1 H), 7.32 (dt, 7.6 Hz, 1.5 Hz, 1 H), 7.61 (dd, 7.6 Hz, 1.5 Hz). MS (API-ES,pos) m/z = 259 [M+H]+

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 2-Methoxyphenylacetate, and friends who are interested can also refer to it.

Reference:
Patent; ABBOTT GMBH & CO. KG; WO2008/25736; (2008); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics