Month: August 2021

Some common heterocyclic compound, 1245643-11-1, name is Methyl 3,4-diamino-5-bromobenzoate, molecular formula is C8H9BrN2O2, 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. Quality Control of Methyl 3,4-diamino-5-bromobenzoate

At -40C, 2,2-dihydroxy-acetic acid (85.61 g; 93Ommol) in H20 (35 mL) was added dropwise to a solution of methyl-3,4-diamino-5-bromobenzoate (190 g; 775.28 mmol) in MeOH (2 L). Then, the reaction mixture was allowed to warm to rt and stirred for2h. The solid was filtered, washed with Et20 and dried under vacuum to give 214 g (98%) of a mixture of two intermediates la and lb (ratio 85/l5 by 1H NMR).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1245643-11-1, its application will become more common.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; ANGIBAUD, Patrick, Rene; QUEROLLE, Olivier, Alexis, Georges; BERTHELOT, Didier, Jean-Claude; MEYER, Christophe; WILLOT, Matthieu, Philippe, Victor; MEERPOEL, Lieven; (384 pag.)WO2017/60406; (2017); A1;,
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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. 17100-63-9, name is Methyl 4-bromo-3-methoxybenzoate, A new synthetic method of this compound is introduced below., Recommanded Product: Methyl 4-bromo-3-methoxybenzoate

To a stirred solution of methyl 4-bromo-3-methoxybenzoate (11.2 g) in THF (130 mL), methanol (45 mL) and water (45 mL) was added a 1 M solution of lithium hydroxide in water (140 mL). The mixture was stirred at room temperature for 1 h. The solvent was removed in vacuum. Water was added and 1 N hydrochloric acid was added with ice bath cooling until pH 4 was reached. The precipitated solid was collected by filtration, washed with water and dried in vacuum to give 10.1 g of the title compound, that was used without further purification. 1H-NMR (300MHz, DMSO-d6): delta [ppm] = 3.87 (s, 3H), 7.42 (dd, 1 H), 7.50 (d, 1 H), 7.68 (d, 1 H), 13.21 (br. s., 1 H).

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; BAYER PHARMA AKTIENGESELLSCHAFT; SCHULZE, Volker; MAIS, Franz-Josef; WO2014/9219; (2014); A1;,
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Application of 24398-88-7, 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. 24398-88-7, name is Ethyl 3-bromobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Production Example 13 To a mixture of 85 mg of palladium acetate, 350 mg of 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl and 15 mL of toluene were added 1.8 mL of ethyl 3-bromobenzoate, 1.02 g of 2-nitroaniline and 4.81 g of cesium carbonate, followed by stirring at 110 C. for 5 hours. The reaction solution was allowed to cool, 50 mL of ethyl acetate was added thereto to remove insoluble materials, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: ethyl acetate-hexane=1:9) to obtain 2.10 g of ethyl 3-[(2-nitrophenyl)amino]benzoate as an light orange oily substance.

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 3-bromobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Furutani, Takashi; Enjo, Kentaro; Kikuchi, Aya; Kuromitsu, Sadao; Ideyama, Yukitaka; Suzuki, Tomoyuki; Kurihara, Ryoko; US2011/282066; (2011); A1;,
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Reference of 87808-49-9, 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. 87808-49-9, name is Methyl 2-bromo-4-methylbenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 1: Preparation of 2-(2-bromo-4-methylphenyl)propan-2-ol To a solution of methyl 2-bromo-4-methylbenzoate (4 g, 18 mmol) cooled at 0 C. was added methylmagnesium bromide (17.5 ml, 52.6 mmol) dropwise. The mixture was allowed to warm to rt and stirred overnight. Then it was quenched with aq. NH4Cl and extracted with ethyl acetate. The organic layer was dried over Na2SO4 and concentrated to provide the product (3.5 g, yield 85%). TLC analysis (silica gel plate, EA_PE=10%): Rf=0.5.

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-bromo-4-methylbenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Anacor Pharmaceuticals, Inc.; Eli Lilly and Company; AKAMA, Tsutomu; Balko, Terry William; Defauw, Jean Marie; Plattner, Jacob J.; White, William Hunter; Winkle, Joseph Raymond; Zhang, Yong-Kang; Zhou, Yasheen; US2013/131017; (2013); A1;,
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Application of 148547-19-7, 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. 148547-19-7, name is Methyl 4-bromo-3-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows.

[00156] Step 1 : To a solution of methyl 4-bromo-3-methylbenzoate (50 g, 219 mmol) in THF (500 mL) at 0 C was added lithium aluminum hydride (262 mL of 1 M solution in THF, 262 mmol) over 15 min. After stirring for 20 min, water (50 mL) was added dropwise, followed by 1 M NaOH (50 mL), and water (50 mL). The reaction mixture was filtered through Celite and concentrated in vacuo. The resulting residue was azeotroped once with toluene, then dissolved in DCM, dried over Na2S04, filtered and the solvent removed in vacuo to provide (4-bromo-3-methylphenyl)methanol as a colorless solid (42 g, 96% yield). XH NMR (400 MHz, DMSO-i¾) delta 7.51 (d, J= 8.1 Hz, 1H), 7.29 (s, 1H), 7.07 (d, J= 8.1 Hz, 1H), 5.23 (t, J= 5.7 Hz, 1H), 4.44 (d, J= 5.7 Hz, 2H), 2.33 (s, 3H).

The chemical industry reduces the impact on the environment during synthesis Methyl 4-bromo-3-methylbenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; CHARRIER, Jean-Damien; BINCH, Haley, Marie; HURLEY, Dennis, James; CLEVELAND, Thomas; JOSHI, Pramod; FANNING, Lev Tyler, Dewey; PINDER, Joanne; O’DONNELL, Michael; VIRANI, Anisa, Nizarali; KNEGTEL, Ronald, Marcellus Alphonsus; DURRANT, Steven, John; YOUNG, Stephen, Clinton; PIERRE-HENRI; KAY, David; REAPER, Philip, Michael; WO2011/143426; (2011); A1;,
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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. 2967-66-0, name is Methyl 4-(trifluoromethyl)benzoate, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 2967-66-0

General procedure: Pathway A-Hydrazine hydrate 64% (v/v) (30.0 mL, 0.33 mol) was heated up to 50-60 C. The methyl ester previously isolated (0.01 mol) was added and the mixture was refluxed during 10 min. The cooling down was proceeded sequentially in a water bath, followed by ice bath and dry ice – ethanol bath. The solid was filtered and washed with cold water. Different conditions were needed to obtain 4-nitro-3-(trifluoromethyl)benzhydrazide (3d) and 4-nitrobenzhydrazide (3 h). Hydrazine hydrate 64% (v/v) (30.0 mL, 0.33 mol) was cooled down in ice bath to -3 to 2 C. The respective methyl ester (0.01 mol) was added and the mixture was stirred during 1 hour. The cooling down was proceeded in dry ice – ethanol bath. The solid was filtered and washed with cold water. Pathway B-each substituted benzoic acid (0.01 mol) was refluxed during 4 h in 20.0 mL (0.50 mol) of anhydrous methanol and 0.5 mL (1.0 mmol) of sulfuric acid. The reaction mixture was cooled down to room temperature. and the hydrazine hydrate 80% (v/v) (10.0 mL, 0.11 mol) was added. The system was maintained into vigorously stirring for more 30 minutes. In the case of compounds with 4-nitro and 4-nitro-3-trifluoromethyl substituent groups attached in the benzene moiety, after the addition of hydrazine hydrate 80% (v/v) at room temperature, the reaction mixture was cooled down in ice bath and maintained into stirring during 1 hour. After these periods, the mixture was maintained at cold temperature to give 3.

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 2967-66-0.

Reference:
Article; Jorge, Salomao Doria; Palace-Berl, Fanny; Masunari, Andrea; Cechinel, Cleber Andre; Ishii, Marina; Pasqualoto, Kerly Fernanda Mesquita; Tavares, Leoberto Costa; Bioorganic and Medicinal Chemistry; vol. 19; 16; (2011); p. 5031 – 5038;,
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Reference of 7686-78-4,Some common heterocyclic compound, 7686-78-4, name is Diethyl 2-vinylcyclopropane-1,1-dicarboxylate, molecular formula is C11H16O4, 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 preparation method is:In an air atmosphere,Add 0.2 mmol of N-pyrimidindolline compound to the microwave reaction tube,0.4mmol of ethylene cyclopropane compound,0.003mmol of [Ru (p-cymene) Cl2] 2,0.04mmol are trimethylbenzoic acid,0.02mmol of silver hexafluoroantimonate, microwave reaction at 25 C for 2 hours;After completion of the reaction, rinse with ethyl acetate.Chromatographic separation after concentration under reduced pressure (silica gel 200-300 mesh, eluent: ethyl acetate / petroleum ether gradient elution, ratio from 0/100 to 100/0),Dried to a pale yellow oil,Yield: 70%, E / Z = 20: 1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Diethyl 2-vinylcyclopropane-1,1-dicarboxylate, its application will become more common.

Reference:
Patent; Zhengzhou University; Henan Communication Polytechnic College; Zhu Xinju; Wang Qiuling; Xie Xiaona; Zhang Xiaojie; Yan Jing; Xu Yan; Hao Xinqi; Song Maoping; (15 pag.)CN110551106; (2019); A;,
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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. 1186-73-8, name is Trimethyl methanetricarboxylate, This compound has unique chemical properties. The synthetic route is as follows., category: esters-buliding-blocks

The intermediate N-(l-methyl-6,7-dihydrocyclohepta[fJindol-5(lH)-ylidene)prop-2-en- 1 -amine obtained above (ca. 8.46 mmol) and trimethyl methanetricarboxylate (2.75 g, 14.46 mmol) were mixed together in PI12O (17 mL). With stirring, the mixture was placed onto a pre-heated heat block at 230 C and heated for 10 min after the initial bubbling of MeOH was observed (occurs at -160 C internal reaction temperature). The reaction mixture was cooled to room temperature, then purified by column chromatography (hexanes, followed by EtOAc/hexanes 0-80% gradient) to provide the product as a yellow solid (2.15 g, 56% overall). ^ MR ^OO MHz, CHCl3-i/) 8 ppm 2.1 1 (ddd, J=14.1, 5.8, 2.0 Hz, 1 H) 3.51 (dd, J=14.1, 8.0 Hz, 1 H) 3.86 (s, 3 H) 4.01 (s, 3 H) 4.38 (dd, J=15.1, 5.9 Hz, 1 H) 4.53 (ddt, J=15.1, 4.6, 2.1 Hz, 1 H) 4.75 (dd, J=17.2, 1.1 Hz, 1 H) 5.05 (dd, J=10.4, 1.1 Hz, 1 H) 5.90 (dddd, J=17.2, 10.4, 5.9, 4.6 Hz, 1 H) 6.37 (ddd, J=9.8, 8.0, 5.8 Hz, 1 H) 6.53 (dd, J=3.2, 0.9 Hz, 1 H) 6.76 (dd, J=9.8, 2.0 Hz, 1 H) 7.20 (d, J=3.2 Hz, 1 H) 7.29 (s, 1 H) 7.85 (s, 1 H) 13.72 (br. s., 1 H). LC-MS 375.3 [M+H]+, 377.3 [M+H]+, RT 1.40 min.

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 1186-73-8.

Reference:
Patent; PTC THERAPEUTICS, INC.; BRANSTROM, Arthur; JOSYULA, Vara Prasad, Venkata Nagendra; ARNOLD, Michael, Andrew; GERASYUTO, Aleksey, I.; KARP, Gary; WANG, Jiashi; WO2013/33228; (2013); A1;,
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Synthetic Route of 107317-58-8, 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. 107317-58-8, name is Methyl 4-bromo-3-(trifluoromethyl)benzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of the product from Step A (17.3 g, 61.2 mmol) in 1,4-dioxane is added A- (4,4,5, 5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-buty ester (18.9 g, 61.2 mmol), 2 M aqueous potassium carbonate (61.2 mL, 122 mmol), and tetrakistriphenylphosphinepalladium(O) (7.07g, 6.10 mmol). The reaction vessel is sealed and heated to 140 C for 4 hours. The mixture is cooled to room temperature and the dioxane is removed in vacuo. The resulting residue is diluted with water and ethyl acetate, filtered to remove insoluble material, and the layers are separated. The aqueous layer is extracted twice with ethyl acetate and the combined organics are dried over Na2SO4, filtered, and the solvent is removed in vacuo. The brown residue is then passed through a short bed of silica rinsing first with 10% ethyl acetate in hexane, then 20% ethyl acetate in hexane. The material collected from the 20% ethyl acetate fraction is evaporated to afford the desired product as a light yellow solid (19.6 g, 83%). LCMS: 371.51 (M+CEta3CN-56).

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 4-bromo-3-(trifluoromethyl)benzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG; BENTZIEN, Joerg, Martin; BOYER, Stephen, James; BURKE, Jennifer; ELDRUP, Anne, Bettina; GUO, Xin; HUBER, John, David; KIRRANE, Thomas, Martin; SOLEYMANZADEH, Fariba; SWINAMER, Alan, David; WO2010/5783; (2010); A1;,
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Adding a certain compound to certain chemical reactions, such as: 1459-93-4, name is Dimethyl isophthalate, 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 1459-93-4, name: Dimethyl isophthalate

6.0 kg of dimethyl isophthalate, 21.0 kg of 2,2,6,6-tetramethyl-4-aminopiperidine was added to a 50 liter reactorIn the reactor all the materials off the entrance. The reaction was carried out at 190 C for 2 hours and then at 230 C for 5 hours. The temperature was lowered to below 180 C, and excess 2,2,6,6-tetramethyl-4-aminopiperidine was recovered by vacuum distillation under a vacuum pump. Then use water to generateN, N’-bis (2,2,6,6-tetramethyl-4-piperidinyl) -1,3-benzenedicarboxamide, filtered and dried to give 12.8 kg of acicular white crystalline product , Yield 93.5%.

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, Dimethyl isophthalate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Xiangtan University; Luo Zhiqiang; Zhang Lingjun; Zhang Jing; Ji Yongsheng; Ji Changfu; Zeng Yang; Liu Mengyan; Zhou Ji; Liu Minna; Wang Zhe; (7 pag.)CN106905225; (2017); A;,
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