Month: May 2021

Synthetic Route of 18927-05-4, 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. 18927-05-4, name is Methyl 3-Methoxyphenylacetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of sodium hydride (13.2 g, 303.6 mmol) in dimethylformamide (350 mL) was added methyl 3-methoxyphenylacetate (25 g, 138 mmol) and methyl acrylate (31 ml, 345 mmol) in dimethylformamide (160 mL) at 0C, then the reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was poured into aqueous hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtrated, and concentrated in vacuo. The residue was purified by silica gel chromatography to give 42.8 g of the title compound as a colorless oil. High-performance liquid chromatography/mass spectrometry m/z 321(M+H) Retention time: 3.61 min.

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

Reference:
Patent; Dainippon Sumitomo Pharma Co., Ltd.; EP1679069; (2006); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 15963-40-3, The chemical industry reduces the impact on the environment during synthesis 15963-40-3, name is Methyl 3-methylenecyclobutanecarboxylate, I believe this compound will play a more active role in future production and life.

To a solution of Et2Zn (11.89 mL, 11.89 mmol) in DCM (10 mL) was added a solution of TFA (0.88 mL, 11.89 mmol) in DCM (10 mL) dropwise at 0 C for 30 minutes. A solution of CH2I2 (0.96 mL, 11.89 mmol) in DCM (10 mL) was added dropwise at 0 C for 45 minutes. The reaction mixture was stirred at 0 C for 1 hour. A solution of methyl 3- methylenecyclobutanecarboxylate (500 mg, 3.96 mmol) in DCM (5 mL) was added to the reaction mixture. The reaction mixture was allowed to warm to 15 C for 16 hours. Saturated NH4CI solution (50 mL) was added to the reaction mixture and the mixture was extracted with DCM (50 mL c 2). The combined organic layers were dried over anhydrous Na2S04, filtered and concentrated. The crude residue was purified by silica gel column chromatography (10 % EtOAc in petroleum ether) to afford the title compound (400 mg, 72 %) as a yellow oil. ‘ H NMR (400 MHz, CDCl3) d 3.71 (s, 3H), 3.34 – 3.27 (m, 1H), 2.53 – 2.48 (m, 2H), 2.26 – 2.20 (m, 2H), 0.49 – 0.42 (m, 4H).

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

Reference:
Patent; GENENTECH, INC.; F. HOFFMANN-LA ROCHE AG; CUNNINGHAM, Christian; BEROZA, Paul Powell; CRAWFORD, James John; LEE, Wendy; RENE, Olivier; ZBIEG, Jason Robert; LIAO, Jiangpeng; WANG, Tao; YU, Chen; (208 pag.)WO2020/51099; (2020); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 27007-53-0, These common heterocyclic compound, 27007-53-0, name is Methyl 2-bromo-5-chlorobenzoate, 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.

Step 2. methyl 5-chloro-2-cyanobenzoate To a stirred solution of methyl 2-bromo-5-chlorobenzoate (11.5 g, 46 mmol) in degassed DMF (50 mL) was added zinc cyanide (2.82 g, 24.0 mmol) and palladium tetrakis-triphenylphosphine (1.0 g, 0.86 mmol) and the mixture was heated to 90 C. for 18 h. The reaction was partitioned between EtOAc (200 mL) and water (100 mL). The organic phase was concentrated in vacuo and the residue was purified by flash chromatography eluding with a gradient of 10%, 15%, 20% ethyl acetate in hexane yielding methyl 5-chloro-2-cyanobenzoate as a white solid (8.0 g, 88% yield). TLC Rf=0.4 (15% EtOAc-hexanes); HPLC RT=3.13 min (Method A); 1H NMR (CDCl3, 400 MHz) 8.13 ppm (d, 1H, J=1.83 Hz); 8.09 ppm (d, 1H, J=8.24 Hz); 7.29 ppm (dd, 1H, J=8.34, 2.10 Hz); 4.02 ppm (s, 3H). Step. 3 2-aminomethyl-5-chlorobenzyl Alcohol

The synthetic route of 27007-53-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Williams, Peter D.; Lyle, Terry A.; Morrissette, Matthew M.; Tran, Lekhanh O.; Staas, Donnette D.; US2003/13700; (2003); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 541-16-2, A common heterocyclic compound, 541-16-2, name is Di-tert-Butyl malonate, molecular formula is C11H20O4, 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.

General procedure: A mixture of 2-(3, 4-dichlorophenyl)acetonitrile (5 mmol), ditert-butyl malonate (3 mmol), and Fe(ClO4)3·H2O (5 mol%) wasplaced in a round-bottomed flask. Then, the reaction mixturewas heated at 80 C for 5 h. After completion of the reactionmonitored by thin layer chromatography (TLC), water (10 mL)was added and the reaction mixture was extracted with ethylacetate (3 × 20 mL). The organic layers were collected, combined,washed with water (3 × 20 ml), dried over anhydrousNa2SO4, and concentrated under vacuum. The pure product wasobtained by directly passing through a silica gel (200-300mesh) column to give a white powder 1m (1.08 g, 84% yield).Compound 1m1H NMR (400 MHz, CDCl3): delta = 7.41-7.35 (m, 2 H), 7.12-7.10 (m,1 H), 5.31 (s, 1 H), 3.40 (s, 2 H), 1.32 (s, 9 H) ppm. 13C NMR (100MHz, CDCl3): delta = 168.9, 135.6, 132.7, 131.2, 131.2, 130.6, 128.6,51.6, 43.5, 28.7 ppm. HRMS: m/z calcd for C12H15Cl2NO [M + H]+:259.0531; found: 259.0533.

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:
Article; Feng, Chengliang; Yan, Bin; Yin, Guibo; Chen, Junqing; Ji, Min; Synlett; vol. 29; 17; (2018); p. 2257 – 2264;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 1195768-18-3, 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. 1195768-18-3 name is Methyl 3-amino-2-fluorobenzoate, 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.

To an ice-cold solution of (2S,4R)-l-(tert-butoxycarbonyl)-4-fluoropyrrolidine-2- carboxylic acid (1.24 g) in DCM (25 mL), was added l-chloro-N,N,2-trimethylprop-l-en-l- amine (0.845 mL, 1.2 equiv) dropwise with stirring. The stirring was continued for 3 hours at this temperature. Methyl 3-amino-2-fluorobenzoate (0.9 g) was then added followed by DIEA (2.78 mL, 3 equiv). The cooling bath was removed and the reaction mixture was stirred overnight at rt. The solvent was co-evaporated with MeOH (3 mL). The remaining residue was then dissolved in chloroform (30 mL) and washed successively with cold 1 N aq HC1 (3 x 20 mL), water (30 mL), and a saturated aq NaHCCb solution (30 mL). The organic layer was dried (Na2S04) and concentrated under reduced pressure to afford the title compound as an amber oil. Used without purification for the next step.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 3-amino-2-fluorobenzoate, and friends who are interested can also refer to it.

Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason, Allan; PHADKE, Avinash, S.; DESHPANDE, Milind; AGARWAL, Atul; CHEN, Dawei; GADHACHANDA, Venkat, Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; GREENLEE, William; (447 pag.)WO2017/35408; (2017); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 35120-18-4, A common heterocyclic compound, 35120-18-4, name is Ethyl 1-bromocyclobutanecarboxylate, molecular formula is C7H11BrO2, 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 solution of 6-methoxyquinoline-4-thiol 4b (477 mg, 2.5 mmol), ethyl 1-bromo cyclobutanecarboxylate (620 mg, 2.9 mmol) and cesium carbonate (326 mg, 7.5 mmol) Was added to 10 mL of N, N-dimethylformamide. The reaction solution was heated to 60 DEG C and stirred for 2 hours. 50 ml of water was added to the reaction solution, and the mixture was extracted with ethyl acetate (50 ml x 4). The organic phases were combined, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to give the title compound ethyl 1 – ((6-methoxyquinolin-4-yl) thio) cyclobutanecarboxylate 4c (620 mg, brown oil), yield: 78%.

The synthetic route of 35120-18-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Hengrui Pharmaceutical Co., Ltd; Jiangsu Hengrui Medicine Co.,Ltd.; Peng, Jian Biao; Sun, Pia Ohyang; Lan, Jiong; Koo, Cheon Yang; Lee, Siaotao; Liu, Bonnian; Han, Quanzhou; Hoo, Kwiye; Jean, Pang Pang; Dong, Qing; Cao, Guo Qing; (67 pag.)KR2016/6207; (2016); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 474709-71-2,Some common heterocyclic compound, 474709-71-2, name is Ethyl 4-bromo-2-fluorobenzoate, molecular formula is C9H8BrFO2, 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 solution LHMDS (38 mL, 1 M solution) in THF (40 mL) cooled to -78C, was added acetonitrile (2.1 mL, 40.5 mmol) drop-wise. The reaction was stirred at -78C for 60 min, and a solution of ethyl 4-bromo-2-fluorobenzoate (Example 286, 5 g, 20.2 mmol) in THF (10 mL) was added. The reaction mixture was left to warm to rt over 16 h. Then, NH4CI (50 mL, 10% aqueous solution) was added, and the organic solvent was removed under reduced pressure. The resulting aqueous suspension was filtered, and the filter cake was washed successively with water and ether, and then dried under mechanical vacuum at 40C to give the desired product (4.4 g). EI-MS m/z [M+Hf 241.2, GCMS RT 12.64 min.

The synthetic route of 474709-71-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMACEUTICALS CORPORATION; WO2006/34491; (2006); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 6279-86-3,Some common heterocyclic compound, 6279-86-3, name is Triethyl methanetricarboxylate, molecular formula is C10H16O6, 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: To a solution of carbonyl compound (1.0-2.0 equiv) in CH2Cl2 or 1,2-dichloroethane, Tf2CHCH2CHTf2(5, 0.50 mmol) was added at room temperature. After stirring at room temperature to 80 C, the reaction mixture was concentrated under reduced pressure. The resultant residue was purified by bulb-to-bulb distillation using a Kugelrohr oven to give bis(triflyl)ethylated product 4.

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

Reference:
Article; Yanai, Hikaru; Fujita, Masaya; Takahashi, Arata; Zhang, Min; Mishima, Masaaki; Kotani, Akira; Matsumoto, Takashi; Taguchi, Takeo; Molecules; vol. 18; 12; (2013); p. 15531 – 15540;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 53518-15-3, name is 7-Amino-4-(trifluoromethyl)-2H-chromen-2-one, 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. HPLC of Formula: C10H6F3NO2

EXAMPLE 61 Preparation of 7-[N’-(3,5-diaminopyrazol-4-ylidene)hydrazino]-4-trifluoromethylchroman-2-one In a manner similar to that described in Example 2, 7-[N’-(3,5-diaminopyrazol-4-ylidene)hydrazino]-4-trifluoromethylchroman-2-one was prepared from 7-amino-4-trifluoromethylchromen-2-one (0.25 g), malononitrile (0.15 g) and hydrazine hydrate (0.3 mL). The title compound (0.101 g) was isolated after purification by column chromatography.

The synthetic route of 7-Amino-4-(trifluoromethyl)-2H-chromen-2-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhang, Zaihui; Daynard, Timothy Scott; Sviridov, Serguei V.; Chafeev, Mikhail A.; Wang, Shisen; US2003/60453; (2003); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 176694-36-3, 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. 176694-36-3, name is Methyl 4-fluoro-3-(trifluoromethyl)benzoate, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of methyl 4-fluoro-3-(trifluoromethyl)benzoate (9.60 g, 43.2 mmol) in N,N-dimethylformamide (100 mL) was added mercaptan sodium (3.33 g, 47.5 mmol) at 0 C. by small portions, and the resulting mixture was stirred at room temperature for 2 hr. The reaction mixture was diluted with ethyl acetate, washed twice with water and once with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was recrystallized from hexane to give the title compound (10.1 g, yield 93%) as colorless crystals.melting point 76-77 C.1H NMR (CDCl3) delta 2.57 (3H, s), 3.94 (3H, s), 7.36 (1H, d, J=8.3 Hz), 8.11 (1H, dd, J=1.9, 8.3 Hz), 8.27 (1H, d, J=1.9 Hz).Elemental analysis (for C10H9F3O2S)Calculated (%): C, 48.00; H, 3.63.Found (%): C, 47.97; H, 3.62.

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

Reference:
Patent; Itoh, Fumio; US2010/69381; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics