Author: Jessica.F

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;,
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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;,
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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;,
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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;,
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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;,
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Application of 2065-23-8, The chemical industry reduces the impact on the environment during synthesis 2065-23-8, name is Methyl 2-phenoxyacetate, I believe this compound will play a more active role in future production and life.

167.87 g of 99% methyl phenoxyacetate (1 mol), 1.26 g of 99% zinc chloride and 1.68 g of 99% 2,4,6-trimethyldiphenyl sulfide were successively added to a 500 mL four-necked flask.154.69g of 99% chlorine gas (2.16mol) was introduced at -20 C, and the reaction was allowed to stand for 30 min, and the fraction of 140-150 C was distilled under a pressure of 1 kpa to obtain methyl 2,4-dichlorophenoxyacetate. 236.21 g, content 98.8%, yield 99.28% based on methyl phenoxyacetate.

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

Reference:
Patent; Shandong Runbo Biological Technology Co., Ltd.; Sun Guoqing; Hou Yongsheng; Zhang Liguo; Chi Zhilong; Hu Yishan; (14 pag.)CN108947821; (2018); A;,
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Electric Literature of 14062-18-1, These common heterocyclic compound, 14062-18-1, name is Ethyl 2-(4-methoxyphenyl)acetate, 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.

Sodium hydride (60% in oil) (467 mg, 11.7 mmol) was added to a benzene solution (10 ml) of ethyl 4-methoxyphenyl acetate (2.0 g, 10.3 mmol), while being cooled with ice. The mixture was stirred at room temperature for 5 minutes. The stirred mixture was cooled with ice again; ethyl formate (1.02 ml, 12.6 mmol) was added thereto and stirred at room temperature for 3 hours. While being cooled with ice, water and ethyl acetate were added to the reaction mixture, and then 2N hydrochloric acid (6 ml) was added to separate the reaction mixture into two layers. The organic layer was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate = 4:1). The purified product was concentrated under reduced pressure to thereby obtain 1.97 g of slightly reddish-brown oily ethyl alpha-(hydroxymethylene)-4-methoxyphenyl acetate (yield: 86%). The resulting object was purged with nitrogen and stored in a freezer. 1H-NMR (CDCl3) deltappm: 1.28 (3H, t, J = 7.1 Hz), 3.81 (3H, s), 4.28 (2H, q, J = 7.1 Hz) , 6.87 (2H, d, J = 8.8 Hz), 7-7.26 (3H, m), 12.02 (1H, d, J = 12.5 Hz).

The synthetic route of 14062-18-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Otsuka Pharmaceutical Co., Ltd.; EP2364706; (2011); A1;,
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Electric Literature of 55666-43-8,Some common heterocyclic compound, 55666-43-8, name is tert-Butyl 3-bromopropanoate, molecular formula is C7H13BrO2, 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 2,2,2-trifluoro-N-(trans-2-phenylcyclopropyl)-N-(piperidin-4-ylmethyl)acetamide (300 mg, 0.919 mmol) in acetonitrile (10 mL) was added potassium carbonate (381 mg, 2.76 mmol) followed by tert-butyl 3-bromopropanoate (211 mg, 1.011 mmol) was heated in a seal tube at 80 C. for 4 hours. The reaction mixture was filtered, and the filtrate evaporated to dryness. The resulting oil was dissolved in 2 ml of EtOH and 2 ml of 1 M NaOH. The reaction mixture was stirred for 20 min. The solution injected on a preparatory HPLC (2 to 10% AcCN: H2O with 0.1% formic acid modifier). The fractions were collected. To each fraction was added 0.1 ml of 6 M HCl, and the fractions were evaporated to dryness. Acid was formed by deprotection of t-butyl during evaporation. 3-(4-(((trans-2-phenylcyclopropyl)amino)methyl)piperidin-1-yl)propanoic acid (140 mg, 0.354 mmol, 38.5% yield) was isolated as yellow oil. 1H NMR (400 MHz, METHANOL-d4) delta 7.29-7.37 (m, 2H), 7.11-7.29 (m, 3H), 3.65 (br. s., 2H), 3.45 (t, J=7.07 Hz, 2H), 3.23 (d, J=5.81 Hz, 2H), 3.11 (br. s., 2H), 3.04 (dt, J=4.01, 7.89 Hz, 1H), 2.90 (t, J=7.07 Hz, 2H), 2.62 (ddd, J=3.54, 6.63, 10.29 Hz, 1H), 2.04-2.29 (m, 3H), 1.70 (dd, 2H), 1.62 (ddd, J=4.42, 6.51, 10.55 Hz, 1H), 1.42 (q, J=6.91 Hz, 1H); LC-MS Rt=0.42 min; MS (ESI): 303.3 [M+H]+.

The synthetic route of 55666-43-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GlaxoSmithKline Intellectual Property (No. 2) Limited; Johnson, Neil W.; Kasparec, Jiri; Rouse, Meagan B.; Tian, Xinrong; Miller, William Henry; Suarez, Dominic; (79 pag.)US9346840; (2016); B2;,
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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. 73792-08-2, name is Methyl 4-amino-2-fluorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 73792-08-2

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride was added to a pyridine (500 ml) solution of 18.9 g of methyl 4-amino-2-fluorobenzoate and 16.5 g of picolinic acid, and stirred at room temperature for 2 hours. The solvent was evaporated away under reduced pressure, 600 ml of ethyl acetate was added to the residue, the organic layer was washed with aqueous 0.25 N hydrochloric acid solution, aqueous 0.25 N sodium hydroxide solution and saturated saline water, dried, concentrated under reduced pressure, solidified from a mixed solvent of hexane/ethyl acetate, and the solid was taken out through filtration. This was dried under reduced pressure to obtain 28.3 g of the entitled compound as a white solid.

The synthetic route of 73792-08-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BANYU PHARMACEUTICAL CO., LTD.; EP1810969; (2007); A1;,
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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 2318-25-4 as follows. COA of Formula: C7H14ClNO3

To anhydrous ethanol (460 g, 10.0 mol) at -3O0C was bubbled in anhydrous hydrogen chloride until the total weight of 821 g of etaCl/EtOeta solution (44percent (w/w) was obtained.Ethyl cyanoacetate (452 g) was added into the etaCl/EtOeta solution (292 g), the mixture was cooled to ice-salt bath temperature and stirred for 1 hours. The reaction was warmed to room temperature and stood overnight. A white precipitate of 102 was obtained and this mixture was used directly in the next step.The obtained mixture was added to a mixture of ether and a solution OfK2COs (828 g) in water (2500 mL). The ether layer was separated, dried over Na2SO4, and filtered. The filtrate was concentrated under reduced pressure to give compound 103 (445 g) as a colorless oil.A mixture of compound 103 (445 g) and ammonium chloride (149.5 g) in ethanol (1500 mL) was heated to reflux for 8 h. The solid was isolated and the filtrate was concentrated. The residue was washed with ether and acetone to give product 104 (220 g, 33percent total yield in three steps). LCMS: 131 [M+l]+, 1H NMR (DMSO-J6): delta 1.22 (t, J= 6.9 Hz, 3H), 3.68 (s, 2H), 4.16 (q, J= 6.9 Hz, 2H), 9.04 (s, 2H), 9.32 (s, 2H).

According to the analysis of related databases, 2318-25-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CURIS, INC.; WO2008/33747; (2008); A2;,
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