Month: March 2021

Application of 17100-65-1, 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. 17100-65-1 name is Methyl 2-bromo-4-methoxybenzoate, 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.

A stirred solution of 2-Bromo-4-methoxy-benzoic acid methyl ester (6) (2.5 g, 10.201 mmol) in DMF (15 mL) was degassed for 15 minutes with argon followed by the addition of Zn(CN)2 (2.39 g, 20.402 mmol) and Pd(PPh3)4 (1.17 g, 1.02 mmol) and the reaction mixture was stirred at 100C for 16 hours. The reaction mixture was diluted with Ethyl acetate, washed with water and brine, dried over sodium sulfate and concentrated. The crude was purified by column chromatography (silica, gradient: 20-30%) EtOAc in Hexane) to afford the Intermediate 7 (900 mg, 46%) as white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 2-bromo-4-methoxybenzoate, and friends who are interested can also refer to it.

Reference:
Patent; THE BROAD INSTITUTE, INC.; THE GENERAL HOSPITAL CORPORATION; INSTITUTO CARLOS SLIM DE LA SALUD; BURNS, Sean, M.; WAGNER, Bridget, K.; VETERE, Amedeo; (189 pag.)WO2018/175324; (2018); A1;,
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Related Products of 25662-28-6, 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. 25662-28-6, name is Methyl 1-cyclopentene-1-carboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Under nitrogen atmosphere, a mixture of in H2O (0.90muL, 0.050mmol) in THF (1mL) was added to an oven-dried reaction tube charged with (R)-H8-BINOL (22.1mg, 0.075mmol). After stirred at RT for 5min, Bu2Mg (1.0M in heptane, 50.0muL, 0.050mmol) and diarylphosphine oxide (3, 0.50mmol, 0.5M in anhydrous THF) were sequentially added and stirred for another 5min before being cooled to-20C. alpha,beta-Unsaturated ester (2, 0.50mmol) was then added, and the reaction was stirred at-20C for 2-3 days. The reaction mixture was quenched with sat. NH4Cl (2mL), diluted with H2O (5mL) and extracted with CH2Cl2 (10mL¡Á2). The combined organic phase was dried over anhydrous Na2SO4. After filtration and concentration, and the residue was purified by silica gel column chromatography (hexane: THF=5:1 to 1:1) to give the corresponding product. The enantiomeric excess was determined by the chiral HPLC analysis.

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

Reference:
Article; Cao, Meng-Yue; Xu, Zhi-Min; Gao, Wei; Liu, Juan; Tan, Fen; Lu, Hai-Hua; Tetrahedron; vol. 75; 24; (2019); p. 3282 – 3291;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 344-14-9, 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. 344-14-9, name is Dimethyl 2-fluoromalonate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Reference Example 1Mixture of dimethyl fluoro[(1R,5R)-5-hydroxycyclopent-2-en-1-yl]propanedioate (8a) and dimethyl fluoro[(1S,5S)-5-hydroxycyclopent-2-en-1-yl]propanedioate (8b) 23.81 g (110.2 mmol) of a 25 w/w % methanol solution of sodium methoxide (NaOMe) was added to a methanol (90.4 mL) solution of 18.19 g (121.2 mmol) of dimethyl fluoropropanedioate (7) over 3 minutes while keeping the internal temperature between 25 C. and 38 C. After stirring the solution thus obtained for 15 minutes, 4.52 g (55.1 mmol) of 6-oxabicyclo [3.1.0] hex-2-ene (6) was added thereto over 2 minutes while keeping the internal temperature between 25 C. and 38 C. After stirring at room temperature for 1 hour, 45 mL of a saturated ammonium chloride aqueous solution was added over 10 minutes while keeping the internal temperature between 26 C. and 35 C. The reaction mixture was concentrated under reduced pressure, most of the methanol was removed by evaporation, and 108 g of a brown solution containing solids was obtained. After extraction with 136 mL of ethyl acetate was carried out twice, washing with 45 mL of water was carried out. After the organic layer was concentrated under reduced pressure, 100 mL of toluene was added, and concentration under reduced pressure was carried out again. The concentrated residue was purified by flash silica gel column chromatography (eluent:toluene/ethyl acetate), thus giving 7.21 g of a mixture of the compound of the formula 8a and the compound of the formula 8b as a yellow oily substance.1H NMR (500 MHz, DMSO-d6): delta (ppm) 2.13-2.17 (m, 1H), 2.56 (dddd, J=2.2, 4.3, 7.1, 17.2 Hz, 1H), 3.32-3.40 (m, 1H), 3.77 (s, 3H), 3.79 (s, 3H), 4.20 (m, 1H), 5.04 (d, J=6.1 Hz, 1H), 5.47 (ddd, J=2.1, 4.3, 6.1 Hz, 1H), 5.85 (ddd, J=2.2, 4.4, 6.1 Hz, 1H). 13C NMR (125 MHz, DMSO-d6): delta (ppm) 41.93, 53.39 (d, J=19.5 Hz), 58.70 (d, J=20.8 Hz), 70.43 (d, J=2.6 Hz), 93.55, 95.14, 125.59, 133.32, 165.42 (d, J=15.6 Hz), 165.62 (d, J=14.3 Hz). 19F NMR (470 MHz, DMSO-d6): delta (ppm) -172.43, -172.36. HRMS(ES)m/z: [M+Na]+ calcd for CHH13O5FNa; 255.0645, found 255.0635. IR (neat) 3528, 3408, 2960, 1755, 1438, 1284, 1253, 1173, 1111, 1068, 1031, 936, 838, 787, 722, 668, 415 cm-1.

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

Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD; US2012/232304; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 10601-80-6, name is Ethyl 3,3-diethoxypropionate, 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 10601-80-6, Application In Synthesis of Ethyl 3,3-diethoxypropionate

General procedure: A mixture of Yb(OTf)3 (2.5 mol%), amine (1.0 eq.), ethyl 3,3-diethoxypropionate (2.5 eq.) and aldehyde (1.1 eq.) in 1,4-dioxane (1.5 mL / 1 eq.) was stirred at 90 C for 6-17 h. After the reaction, the resulting mixture was washed with PBS buffer solution (25 mL) and extracted with CH2Cl2 (15 mL¡Á3). The organic layer was dried over MgSO4. Removal of the solvent in vacuo, followed by chromatography on silica gel column (AcOEt/Hexane or CHCl3/MeOH), afforded dihydropyridine 4.

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

Reference:
Article; Sueki, Shunsuke; Takei, Ryo; Abe, Junya; Shimizu, Isao; Tetrahedron Letters; vol. 52; 34; (2011); p. 4473 – 4477;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 5335-05-7, 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. 5335-05-7 name is Chloromethyl benzoate, 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.

Into 2 ml of N,N-dimethylformamide was suspended 0.05 g of sodium hydride (60% oily), and 0.2 g of 3-(4-trifluoromethylpyridin-2-yl)-l,2,4-oxadiazol-5-one was added at room temperature. After stirring for 10 minutes, 0.18 g of chloromethylbenzoate, and the mixture was stirred at 70C for 3 hours. The reaction solution was allowed to cool to room temperature, and poured into an aqueous saturated ammonium chloride solution, followed by extraction with ethyl acetate three times. The organic layers were combined, washed with an aqueous saturated sodium chloride solution, dried with anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.12 g of [3-(4- trifluoromethylpyridin-2-yl)- 1 ,2,4-oxadiazol-5-on-4-yl]methyl=benzoate (present compound (27)).Present Compound (27)1H-NMR: 6.44 (s, 2H), 7.38-7.42 (m, 2H), 7.53-7.59 (m, IH), 7.71 (d, IH), 7.79-7.92 (m, 2H), 8.30 (s, IH), 8.87 (d, IH)

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

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; WO2009/66786; (2009); A1;,
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. 369-25-5, name is Methyl 3,4-difluorobenzoate, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H6F2O2

[0620] tert-Butyl 4-(2-fluoro-4-(methoxycarbonyl)phenyl)piperazine-l-carboxylate (301): Potassium carbonate (5.56 g, 40.3 mmol) and tert-bvXy piperazine-1-carboxylate (6.92 g, 37.2 mmol) were combined; methyl 3,4-difluorobenzoate (5.33 g, 31.0 mmol) was added, and the reaction mixture was stirred at 900C for 1 d. The mixture was triturated with ethyl acetate (3 x 5 mL) and the combined organic extracts were filtered, concentrated down to about 5-10 mL, and subjected to flash column chromatography on silica gel (120 g SiO2, hexanes:ethyl acetate 1 :0 to 4:1) to afford the title compound as a white solid (4.702 g, 13.90 mmol, 44.9 % yield). ESI-MS: m/z 339 (M+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; TAKEDA PHARMACEUTICAL COMPANY LIMITED; BROWN, Jason, W.; GANGLOFF, Anthony, R.; JENNINGS, Andrew, John; VU, Phong, H.; WO2010/111626; (2010); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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 6279-86-3 as follows. Quality Control of Triethyl methanetricarboxylate

5-ethyl-6-{4-[(3aR,6aR)-hexahydropyrrolo[3,4-b]pyrrol-5(lH)-yl]phenyl}-4-hydroxy-2- oxo-l,2-dihydropyridine-3-carboxylic acid hydrochloride (1:1) (Cpd 246)Step 1:A solution of l-(4-chlorophenyl)butan-l-one (5.00 g, 27.37 mmol) and t-butyl amine(11.60 mL, 109.90 mmol) in DCM (30 mL) was cooled to 0 C. A solution of TiCl4 (1MDCM, 18.00 mL, 18.00 mmol) was added dropwise via syringe pump over 30 min. The reaction mixture was allowed to warm to room temperature and stirred overnight. The mixture was diluted with DCM (200 mL) and then the reaction was quenched with aHC03 (aqueous saturated, 60 mL). After vigorous shaking, the organic phase was separated using a PTFE phase separator, then dried over Na2S04. The solvent was removed to afford a colorless oil (5.30 g, 81), which was used directly in the next step without furtherpurification.The oil (2.14 g, 8.99 mmol) and triethylmethane tricarboxylate (2.20 mL, 10.46 mmol) in diglyme (9 mL) were heated at 160 C for 2 h. After the mixture was cooled to room temperature, a white solid was collected by filtration and washed with Et20. The resulting product (1.54 g, 53%) was obtained as a colorless crystalline material.XH NMR (500 MHz, DMSO-i?) delta ppm 0.95 (t, J=7.4 Hz, 3H) 1.30 (t, J=7.1 Hz, 3H) 2.18 (d, J=7.4 Hz, 2H) 4.34 (q, J=7.1 Hz, 2H) 7.44 (d, J=8.2 Hz, 2H) 7.57 (d, J=8.2 Hz, 2H) 11.43 (br. s., 1H) 13.57 (s, 1H). LC-MS 322.2/324.2 [M+H]+, RT 1.30 min.

According to the analysis of related databases, 6279-86-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PTC THERAPEUTICS, INC.; BRANSTROM, Arthur; JOSYULA, Vara Prasad, Venkata Nagendra; ARNOLD, Michael, Andrew; GERASYUTO, Aleksey, I.; KARP, Gary; WANG, Jiashi; WO2013/33240; (2013); A1;,
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. 107317-58-8, name is Methyl 4-bromo-3-(trifluoromethyl)benzoate, A new synthetic method of this compound is introduced below., Product Details of 107317-58-8

To a mixture of methyl 4-bromo-3-(trifluoromethyl)benzoate (1.00 g, 3.53 mmol), bis(pinacolato)diboron (1.79 g, 7.06 mmol), and KOAc (1.04 g, 10.6 mmol) in DMSO (15 mL) was added Pd(PPh3)4 (816 mg, 0.706 mmol) under N2 atmosphere. Then the mixture was heated to 120C for 3 hours. The reaction mixture was cooled followed by an aqueous/EtOAc workup to give the crude product (2.3 g) as a yellow oil.

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; N30 PHARMACEUTICALS, LLC; SUN, Xicheng; QIU, Jian; STOUT, Adam; WO2012/83165; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 23680-40-2, name is Methyl 3-bromopropiolate, 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. Recommanded Product: Methyl 3-bromopropiolate

Into a 50-mL round-bottom flask, was placed tert-butyl 1H-pyrrole-1-carboxylate (3) (14.4 g, 86.12 mmol, 3.00 equiv), methyl 3-bromoprop-2-ynoate (2) (4.7 g, 28.84 mmol, 1.00 equiv). The resulting solution was stirred for 20 h at 90 C. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:30?1:15) as eluent to furnish 2.89 g (30%) of 7-tert-butyl 2-methyl 3-bromo-7-azabicyclo[2.2.1]hepta-2,5-diene-2,7-dicarboxylate (4) as a yellow oil.

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

Reference:
Patent; YEE, Calvin W.; Li, Zhe; US2015/141465; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 454-31-9, 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. 454-31-9, name is Ethyl 2,2-difluoroacetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Intermediate 16 (3.2 g, 0.0123 mol) was stirred in toluene (150 mL) at 0C under N2. Potassium tert-butoxide (1.94 g, 17.3 mmol) was added at 0-5C, ethyldifluoroacetate (1.84 g, 0.0149 mol) was added dropwise at 0-5C. RM was stirred at RT for 2 hr. The RM was washed with 10% H2S04 in water and the OL was dried on MgS04, filtered and evaporated to yield intermediate 17 (4.16 g, 99%).

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

Reference:
Patent; JANSSEN PHARMACEUTICA NV; VAN ROOSBROECK, Yves, Emiel, Maria; VAN DEN KEYBUS, Frans, Alfons, Maria; TRESADERN, Gary, John; BUIJNSTERS, Peter, Jacobus, Johannes, Antonius; VELTER, Adriana, Ingrid; JACOBY, Edgar; MACDONALD, Gregor, James; GIJSEN, Henricus, Jacobus, Maria; AHNAOU, Abdellah; DRINKENBURG, Wilhelmus, Helena, Ignatius, Maria; (216 pag.)WO2018/83098; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics