Month: August 2021

Electric Literature of 2967-66-0, The chemical industry reduces the impact on the environment during synthesis 2967-66-0, name is Methyl 4-(trifluoromethyl)benzoate, I believe this compound will play a more active role in future production and life.

General procedure: Each substituted benzoic acid (1) (0.02 mol) was refluxed for 4 h in 20.0 mL (0.49 mol) of anhydrous methanol and 0.5 mL (0.01 mol) of sulphuric acid. The reaction mixture was cooled down to room temperature and the hydrazine hydrate 80% (v/v) (10.0 mL, 0.13 mol) was added. The system was maintained by vigorously stirring for more 30 min in reflux. In the case of compound with 4-nitro substituent group attached to 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 h. After this period, the mixture was maintained at low temperature to give 2.19,22

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

Reference:
Article; Palace-Berl, Fanny; Jorge, Saloma?o Do?ria; Pasqualoto, Kerly Fernanda Mesquita; Ferreira, Adilson Kleber; Maria, Durvanei Augusto; Zorzi, Rodrigo Rocha; De Sa? Bortolozzo, Leandro; Lindoso, Jose? A?ngelo Lauletta; Tavares, Leoberto Costa; Bioorganic and Medicinal Chemistry; vol. 21; 17; (2013); p. 5395 – 5406;,
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Reference of 23680-40-2,Some common heterocyclic compound, 23680-40-2, name is Methyl 3-bromopropiolate, molecular formula is C4H3BrO2, 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.

Intermediate 142Cmethyl 2-bromo-5-(diisopentylcarbamoyl)pyrazolo[1 ,5-a]pyridine-3-carboxylateA suspension of /V-aminopyridinium 2,4-(dinitro)phenolate (10 g, 21.67 mmol), methyl 3- bromopropiolate (3.12 ml, 26.0 mmol) and potassium carbonate (5.99 g, 43.3 mmol) in degassed DMF (75 ml) was stirred at 0 C for 5 minutes and at 22 C for 18h. The mixture was diluted with ethyl acetate (100 mL) and washed with water (3 x 25 mL), brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography on silica gel (120g, 0% to 100% ethyl acetate/hexanes over 19 min). to provide methyl 2-bromo-5-(diisopentylcarbamoyl)pyrazolo[1 ,5- a]pyridine-3-carboxylate (0.52 g, 1.186 mmol, 5.47 % yield). LCMS m/z 438.4, 440.1 (M + H)+.

The synthetic route of 23680-40-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITE DE MONTREAL; BOUVIER, Michel; MARINIER, Anne; RUEL, Rejean; RENE , Patricia; CHANTIGNY, Yves; DAGNEAU, Philippe; GINGRAS, Stephane; WO2012/100342; (2012); A1;,
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28170-07-2, name is Benzyl phenyl carbonate, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Safety of Benzyl phenyl carbonate

A mixture of 1,6-diaminohexane 39 (39.15 g, 0.338 mol) and benzyl phenyl carbonate (35.7 g, 0.156 mol) inethanol (125 ml) was stirred for 2 hours at room temperature and subsequently heated for an additional hour atreflux to achieve full conversion. The reaction mixture was allowed to cool to room temperature, affording awhite precipitate. After removing the precipitate by filtration, the supernatant was evaporated to dryness anddissolved in 330 ml 2 M aqueous HCl. The resulting solution was extracted with dichloromethane (DCM)(2×150 ml). The aqueous phase was subsequently adjusted to pH = 10 with 6 M aqueous NaOH and extractedwith DCM (3×150 ml). All organic phases were combined, dried over Na2SO4, evaporated to dryness, anddissolved in 200 ml diethyl ether. The resulting solution was extracted with 1M aqueous NaOH (3×50 ml), driedover Na2SO4, and evaporated to dryness to afford crude 40. The product was recrystallized from diethyl ether at-18C to afford white crystals (12.0 g, 31 %). 1H NMR (400 MHz, CDCl3): delta 1.03 (br.s, 2H), 1.58-1.14 (m, 8H),2.66 (t, J = 6.9 Hz, 2H), 3.18 (q, J = 6.7 Hz, 2H), 4.83 (br.s, 1H), 5.08 (s, 2H), 7.45 – 7.19 (m, 5H) ppm. 13CNMR (400 MHz, CDCl3): delta 26.63, 26.68, 30.07, 33.83, 41.12, 42.25, 66.67, 128.17, 128.21, 128.61, 136.78,156.51 ppm. RP-LCMS: calc. Mw= 250.2 g/mol, found m/z: 251.3 [M+H]+.Synthesis of

The synthetic route of 28170-07-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; De Feijter, Isja; Goor, Olga J. G. M.; Hendrikse, Simone I. S.; Comellas-Aragones, Marta; Soentjens, Serge H. M.; Zaccaria, Sabrina; Fransen, Peter P. K. H.; Peeters, Joris W.; Milroy, Lech-Gustav; Dankers, Patricia Y. W.; Synlett; vol. 26; 19; (2015); p. 2707 – 2713;,
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Electric Literature of 4224-69-5, 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 4224-69-5 as follows.

To a dry nitrogen-flushed 15 mL round bottom flask was added dry THF (5.9 mL) and iPr2NH(0.87 mL, 6.21 mmol, 1.05eq.). The flask was cooled to -78 C andn-BuLi(2.48 mL, 6.21 mmol, 1.05eq.) was added slowly. The mixture wasstirred at 0 C for 10 minutes and then cooled back down to -78 C and cannulated into a -78 C solution of starting material(1.16 g, 5.91 mmol, 1.00eq.) in THF (5.9 mL).The reaction mixture was stirred for 30 min at -78 C and then methyl(2-bromomethyl)acrylate wasadded (0.87 mL, 7.09 mmol,1.20 eq.) via syringe. The reaction wasstirred for 1h at -78 C then 3 h at r.t. The reaction was quenched with H2O(10 mL) and extracted with Et2O (2 x 20 mL). The combinedorganics were washed with brine (10 mL), dried withMgSO4, rotovapped, and chromatographedto yield the desired product was a white solid (1.5338 g, 5.21 mmol) in 88% yield. 1H NMR (300 MHz, CDCl3)delta 8.03 – 7.91 (m, 2H), 7.47-7.38 (m, 1H), 7.36 – 7.13 (m, 7H), 6.07 (s,1H), 5.41 (s, 1H), 4.95 (t, J = 7.2Hz, 1H), 3.71 (s, 3H), 3.23 (dd, J = 14.1, 7.3 Hz, 1H), 2.79 (dd, J = 14.0, 7.2 Hz, 1H).. 13C NMR (75 MHz, CDCl3) delta 198.7, 167.2, 138.7,137.3, 136.5, 132.8, 128.8, 128.6, 128.4, 128.2, 128.0, 127.9, 127.1, 52.2,51.8, 36.7.

According to the analysis of related databases, 4224-69-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Ramachandran, P. Veeraraghavan; Helppi, Matthew A.; Lehmkuhler, Arlie L.; Marchi, Jennifer M.; Schmidt, C. Max; Yip-Schneider, Michele T.; Bioorganic and Medicinal Chemistry Letters; vol. 25; 19; (2015); p. 4270 – 4273;,
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Some common heterocyclic compound, 7149-03-3, name is Ethyl 4-amino-3-bromobenzoate, molecular formula is C9H10BrNO2, 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. Formula: C9H10BrNO2

The title compound was prepared following the procedure described in step-3 of Intermediate-33 by using 2-chloro-4-(4,4,5,5-tetramethyl- 1,3 ,2-dioxaborolan-2-yl)benzonitrile (0.950 g,3.S8mmol), ethyl 4-amino-3-bromobenzoate (step-2 of Intermediate-33, 0.850 g, 3.51 mmol),Pd(dppCi2(O.145 g, 0J77 rnrnoi), diglyme (10 mL), K2C03 (0.728 g, 5.27 mmol) to afford0.720 g of title product. ?H NMR (300 MHz, DMSO-d6): 8.04-8.01(d, J = 8.4Hz, 1H), 7.76(m, 2H), 7.57 (m, 2H), 6.80 (d, 1H), 5.96 (s, 2H), 4.22-4.20 (q, J = 6.9Hz, 2H), 1.28-1.23 (t, J = 6.9Hz, 3H):_To a solution of ethyl 4-amino-3-bromobenzoate (5.0 g, 20.66 mmol), (4- cyanophenyl)boronic acid (3.33 g, 22.72 mmol) and Pd(dppf)C12 (0.843 g, 1.03 mmoi) indiglyme (10 mL) was added K2C03 (4.27 g, 30.99 mmol). The reaction mixture was heated at80C for 4 h. The reaction mass was quenched with water and extracted with EtOAc. The organic layer was washed with water and brine. The organic layer was separated, dried, filtered and concentrated to afford 2.7 g of title product. ?H NMR (300 MHz, DMSO-d6): 7.92-7.89 (d, J = 7.8 Hz, 2H), 7.69-7.67 (d, J = 8.7 Hz, 1H), 7.63-7.60 (d, J = 7.8 Hz, 2H),7.56 (s, 1H), 6.8 1-6.78 (d, J = 8.4Hz, 1H), 5.83 (br s, 2H), 4.22-4.20 (q, J = 6.9 Hz, 2H),1.28-1.23 (t, J= 7.5 Hz, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7149-03-3, its application will become more common.

Reference:
Patent; GLENMARK PHARMACEUTICALS S.A.; GHARAT, Laxmikant Atmaram; MUTHUKAMAN, Nagarajan; PISAL, Dnyandeo; KHAIRATKAR-JOSHI, Neelima; SHAH, Daisy Manish; KADAM, Sheetal R; (303 pag.)WO2016/55947; (2016); A1;,
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Application of 609-12-1, A common heterocyclic compound, 609-12-1, name is Ethyl 2-bromo-3-methylbutanoate, molecular formula is C7H13BrO2, 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.

A solution of 2-bromo-3-methyllpropanoic acid ethyl ester (0.418 g, 2 mmol) and 4-bromobenzylthiol (0.402 g, 2 mmol) in DMF (5 mL) was cooled to 0 C and treated with K2CO3 (0. 414 G, 3. mmol). After stirring for 2 h, the reaction was quenched with 5% HC1 (15 mL) and diluted with ethyl acetate (50 mL). After seperation, the aqueous layer extracted with ethyl acetate (3 x 15 mL). The combined organic layers were washed with sat. aq NACL, dried over MGS04 and concentrated. Purification by flash column chromatography (5% ethyl acetate in heptane) provided (4-bromophen-yl-4-methylsulfanyl)-3- methylbutanoic acid ethyl ester (660 MG, 90%) as white solid. 1H NMR (CDC13), 7.43 (d, J = 8 Hz, 2 H), 7.18 (d, J = 8 Hz, 2 H), 4.17 (q, J = 6 Hz, 2 H), 3.75 (s, 2 H), 2.85 (d, J = 9 Hz, 1 H), 2.04 (m, 1 H), 1.29 (t, J = 6 Hz, 3 H), 1.02 (d, J = 6 Hz, 3 H), 0.98 (d. J = 6 Hz, 3 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; THE INSTITUTE OF PHARMACEUTICAL DISCOVERY, LLC; WO2004/99170; (2004); A2;,
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107317-58-8, name is Methyl 4-bromo-3-(trifluoromethyl)benzoate, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Product Details of 107317-58-8

To a DMF solution (20 mL) of 4-bromo-3-trifluoromethylbenzoic acid methyl ester (1.07 g), copper(I) iodide (720 mg) and fluorosulfonyldifluoroacetic acid methyl ester (4.78 mL) were added, and the mixture was stirred overnight at 90C. The reaction mixture was left to stand to cool to room temperature and filtered through a Celite pad. The filtrate was concentrated under reduced pressure. Saturated brine was added to the residue, followed by extraction thrice, each with ethyl acetate. The extracts were combined and washed with saturated brine, followed by drying over sodium sulfate anhydrate. Insoluble matter was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by flash column chromatography (Yamazen Hi-Flash column 2L), whereby a mixture (632 mg) of the title compound and raw materials were yielded.

The synthetic route of 107317-58-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Daiichi Sankyo Company, Limited; EP2017263; (2009); A1;,
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Electric Literature of 42726-73-8,Some common heterocyclic compound, 42726-73-8, name is tert-Butyl methyl malonate, molecular formula is C8H14O4, 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: alpha-Monosubstituted malonic diester 1 was synthesized according to the reported procedure as follows.3 tert-Butyl methyl malonate was purchased from Kanto Chemical, and used without further purification. The physical properties and spectral data of the new compounds, 2-(2-methylbenzyl)malonate 1g, 2-prenylmalonate 1l, and 2-(2-benzyloxyethyl)malonate 1o, are listed below. A 100 mL round-bottom flask equipped with a stirring bar was charged with tert-butyl methyl malonate (846 muL, 5.0 mmol) and DMF (10 mL). To the solution, sodium hydride (60percent oil suspension, 200 mg, 5.0 mmol) was added. The reaction was allowed to stir at 0 °C for 30 min. To the mixture, corresponding alkyl halide (5.0 mmol) was added at 0 °C and the mixture was stirred at room temperature for 24 h. To the reaction mixture, H2O was added, and the mixture was extracted with CH2Cl2 (3 * 20 mL), dried over MgSO4, and concentrated in vacuo. The remaining residue was purified by silica gel column chromatography (hexane/ethyl acetate) to afford the desired product 1.

The synthetic route of 42726-73-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Odanaka, Yuki; Kanemitsu, Takuya; Iwasaki, Kanako; Mochizuki, Yukiko; Miyazaki, Michiko; Nagata, Kazuhiro; Kato, Masaru; Itoh, Takashi; Tetrahedron; vol. 75; 2; (2019); p. 209 – 219;,
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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. 61644-18-6, name is Chloromethyl isobutyrate, A new synthetic method of this compound is introduced below., Computed Properties of C5H9ClO2

General procedure: Carboxylic acid (±)-9 (5.18 mmol) was dissolved in N,N-dimethylformamide (15.5 mL). Cesium carbonate (4.14 mmol) was added to the solution and the suspension was stirred during 2-3 min after which chloromethyl 2-methylpropanoate (6.73 mmol) was added. After stirring at room temperature during 18-24 h, dichloromethane (30 mL) was added to the mixture and the resulting organic phase was successively washed with water (3×20 mL) and brine (3×20 mL). Organic solvent was eliminated and the residue was submitted to flash chromatography (hexane/ethyl acetate mixtures) to yield the corresponding diester (±)-5.

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; Torres, Susana Y.; Ochoa, Estael; Verdecia, Yamila; Rebolledo, Francisca; Tetrahedron; vol. 70; 31; (2014); p. 4675 – 4684;,
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Electric Literature of 15568-85-1, A common heterocyclic compound, 15568-85-1, name is 5-(Methoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione, molecular formula is C8H10O5, 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 3[00178] To a stirred solution of the l-(3,4-dichloro-phenyl)-ethanone oxime (1 eq) in dry THF (6vol) cooled externally to -15C was added 2.5M n-BuLi (2.2 eq) dropwise. After stirring the reaction mixture for 75 minutes, 5-methoxymethylene- 2,2-dimethyl-[l,3]dioxane-4,6-dione (1.0 eq) in THF (9 vol) was added to the externally cooled reaction mixture. After 1 hour the reaction mixture was warmed to 0C for 15 minutes, and then stirred for 16 hours at room temperature. The reaction mixture was added to water (27vol) and extracted with TBME (2 x 7vol). The aqueous layer was acidified with 5M H2SO4 (3vol) and further extracted with TMBE (3 x 7 vol). The combined organics were filtered and concentrated under reduced pressure to give a crude residue.

The synthetic route of 15568-85-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHDI, INC.; WITYAK, John; TOLEDO-SHERMAN, Leticia, M.; LEEDS, Janet; DOMINGUEZ, Celia; COURTNEY, Stephen, Martin; YARNOLD, Christopher, John; DE AGUIAR PENA, Paula, Cristina; SCHEEL, Andreas; WINKLER, Dirk; WO2010/17132; (2010); A1;,
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