Month: July 2021

4341-76-8, name is Ethyl 2-butynoate, 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 4341-76-8

General procedure: In a 1 dram vial, methyl non-2-ynoate (88 mg, 1.0 equiv), 4-picoline (2.55 muL, 0.05equiv.), half the amount of bis(pinacolato)diboron (198 mg total, 1.5 equiv), and 1 mL of 1.3mg/mL CuSO4 stock solution (0.01 equiv.) are mixed and stirred vigorously at 50 C. The remaining half of bis(pinacolato)diboron is added over a period of 10 minutes. After 3 hours, 1mL of hexanes is added to quench the reaction. The aqueous layer is extracted 3x with hexanes. The hexanes layer is washed 5x with water, dried over sodium sulfate, filtered, and concentrated in vacuo. Column chromatography is used to purify the product.

The synthetic route of 4341-76-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Peck, Cheryl L.; Calderone, Joseph A.; Santos, Webster L.; Synthesis; vol. 47; 15; (2015); p. 2242 – 2248;,
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Some common heterocyclic compound, 2005-10-9, name is 6H-Benzo[c]chromen-6-one, molecular formula is C13H8O2, 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 6H-Benzo[c]chromen-6-one

4′-Bromo-N,N-diphenyl-[1,1′-biphenyl]-4-amine 8 (1.60 g,4.00 mmol) was dissolved in 25 mL of anhydrous THF in an oven dried round bottom flask. The solution was cooled to 78 C in a dry ice/acetone bath and sparged with Ar for 20 min. 2.5 M n-BuLi in hexane (1.60 mL, 4.00 mmol) was added dropwise via syringe and the reaction was stirred for 15 min at 78 C. The cooling bath was removed, and the reaction stirred for 10 min. The reaction was cooled back to 78 C and stirred another 15 min. During this time 6H-benzo[c]chromen-6-one 9 (713 mg, 3.63 mmol) was dissolved in 10 mL of anhydrous THF in a separate oven dried round bottom flask. The solution was cooled to 78 C in a dry ice/acetone bath and sparged with Ar for 10 min. The aryllithium solution was transferred to the solution containing 9 at 78 C via cannula under Ar pressure. The cooling bath was removed, and the reaction stirred for 10 min. The reaction was cooled back to 78 C and stirred another 15 min. The reaction was quenched by the addition of 20 mL of sat. NH4Cl over 10 min at 78 C. The cooling bath was removed, and the reaction was allowed to warm to rt with stirring. 20 mL of water was added, and the mixture was subsequently extracted 3x with 50 mL of EtOAc. The combined organics were washed with brine, dried with Na2SO4, filtered, and concentrated under reduced pressure to yield a crude oily solid. The crude product was purified with column chromatography under gradient elution (10:90 CH2Cl2:hexane/80:20 CH2Cl2:hexane) to yield 17a as a light-yellow powder (750 mg, 40%) but not characterized further. 300 mg (0.580 mmol) of 17a was dissolved in 20 mL of CH2Cl2 in a graduated cylinder and 0.1 mL of a neat 1:1 HBF4 diethyl ether complex and 0.5 mL of Ac2O was carefully added resulting in a blue solution. Diethyl ether (30 mL) was layered on top of the solution and was allowed to sit for 48 h as a ppt formed. The ppt was filtered to achieve a greenish/black solid (273 mg, 80%). The product was acid sensitive and was therefore analyzed via NMR spectroscopy dissolved in CD2Cl2 as a solvent with no added CF3CO2D, which reduced its solubility. mp 226e229 C. 1H NMR (400 MHz,CD2Cl2): d 8.92 (d, J 8.6 Hz, 1H), 8.84 (d, J 8.3 Hz, 1H), 8.78 (d,J 8.1 Hz, 1H), 8.60 (t, J 7.7 Hz, 1H), 8.36 (d, J 8.6 Hz, 2H), 8.27 (d,J 8.3 Hz, 1H), 8.17 (t, J 7.8 Hz, 1H), 8.15-8.02 (m, 4H), 7.73 (br,2H), 7.36 (br, 5H) 7.20 (br, 7H). 13C NMR (100 MHz, CD2Cl2): d 183.4,151.9, 144.1, 139.8, 136.5, 135.2,135.1, 132.6, 131.2, 130.2, 129.1, 128.2,127.5, 126.3, 124.7, 124.6, 124.1, 122.1, 121.0, 120.3. IR (ATR) nmax:1583, 1485, 1050 cm1. HRMS (ESI) m/z calcd for C37H26NO [M]500.2014, found 500.2023.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2005-10-9, its application will become more common.

Reference:
Article; Meyer, Samantha M.; Charlesworth-Seiler, Eva M.; Patrow, Joel G.; Kitzrow, Jonathan P.; Gerlach, Deidra L.; Reinheimer, Eric W.; Dahl, Bart J.; Tetrahedron; vol. 76; 23; (2020);,
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Reference of 69812-51-7, 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. 69812-51-7, name is Methyl 4-chlorosulfonylbenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

The reactions were carried out in a one-neck round bottomask. The corresponding 2-amino-2-methylpropanoic acid (0.88 g,8.5 mmol) and triethylamine (3.4 g, 34 mmol) were added to avigorously stirred mixture of water (5 mL) at 0C. When solidcompletely dissolved in water, 4-chlorosulfonyl benzoic acidmethyl ester (1 g, 4.3 mmol) was added dropwise over 30 min. Thenthe reaction was stirred at rt for 12 h, the product was extractedwith EtOAc (3 50 mL). Combined organic layers were dried overNa2SO4, concentrated in vacuo. The residue was puried by silicagel column chromatography (DCM/MeOH 30/1) to afford thedesired product. Yellow solid, m.p. 170.2e173.6C.1H NMR(400 MHz, DMSO) d 8.24 (s, 1H), 8.10 (d, J 8.4 Hz, 2H), 7.93 (d,J 8.4 Hz, 2H), 3.88 (s, 3H), 1.28 (s, 6H).13C NMR (100 MHz, DMSO)d 175.5, 165.7, 148.0, 132.9, 130.2, 127.0, 58.4, 53.0, 26.2. HRMS (ESI-TOF) m/z Calcd for C12H15NO6S [MNa]324.0518, found 324.0504.

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

Reference:
Article; Liu, Wei; Xu, Xingyu; Zhao, Hongyan; Yan, Xiaoyu; Tetrahedron; vol. 74; 30; (2018); p. 4111 – 4118;,
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Adding a certain compound to certain chemical reactions, such as: 82782-85-2, name is Methyl 4H-thieno[3,2-b]pyrrole-5-carboxylate, 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 82782-85-2, name: Methyl 4H-thieno[3,2-b]pyrrole-5-carboxylate

Compounds e4. Dried K2CO3 (0.15 mol), alkylating agent (0.1 mol) and crown-16 (0.5 mmol) were added to the solution of compound e3 (0.1 mol) in DMF (100 ml). The suspension obtained was stirred at 80-90 C. for 4 hours, cooled to room temperature and poured into 10-fold volume of water. The precipitated solid was filtered off, washed with water, dried in the opened air and recrystallized from ethanol. The oily products were extracted three times with methylene chloride, combined extracts were washed with water, dried over MgSO4 and evaporated at reduced pressure. The residue was recrystallized from ethanol. If required, recrystallization was repeated from the proper solvent. The yield of compounds e4 was 30-75%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 4H-thieno[3,2-b]pyrrole-5-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; ALLA CHEM, LLC; US2011/53915; (2011); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 39149-80-9, The chemical industry reduces the impact on the environment during synthesis 39149-80-9, name is tert-Butyl 2-bromopropanoate, I believe this compound will play a more active role in future production and life.

To a solution of A-4 (200 mg, 0.68 mmol) in DMF (4 mL) was added tert-butyl 2-bromopropanoate (169.98 mg, 0.81 mmol) and CS2CO3 (441.45 mg, 1.35 mmol). The resulting mixture was stirred at 55 C for 2 hours. Saturated NH4C1 aqueous (20 mL) and EtOAc (20 mL) were added to the reaction mixture. After separation, the organic layer was washed with brine (20 mL x 2), dried over anhydrous Na2SC>4, filtered and concentrated to give the crude product that was purified by flash chromatography on silica gel (EtOAc in PE = 0% to 10% to 20%) to afford A-51 (235 mg, 0.55 mmol) as an oil. 1H NMR (CDCI3, 400MHz) deltaH = 7.53 (d, 2H), 7.33 – 7.28 (m, 4H), 7.13 (s, 1H), 5.05 (q, 1H), 1.75 (d, 3H), 1.44 (s, 9H)

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, tert-Butyl 2-bromopropanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PRAXIS PRECISION MEDICINES , INC.; REDDY, Kiran; MARTINEZ BOTELLA, Gabriel; GRIFFIN, Andrew, Mark; MARRON, Brian, Edward; (244 pag.)WO2018/148745; (2018); A1;,
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Adding a certain compound to certain chemical reactions, such as: 3377-20-6, name is Diethyl 2-methylenemalonate, 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 3377-20-6, COA of Formula: C8H12O4

nBuLi solution (2.5 M in hexanes, 2.4 mL, 6.0 mmol) was added, dropwise over 4 min., to a cooled (-20 C bath maintained by an immersion cooler) solution of N,N,N?-trimethylethylenediamine (655 mg, 6.41 mmol) in 2-MeTHF (14 mL). After stirring for 15 min., 4-tert-butoxybenzaldehyde (1.02 g, 5.72 mmol) was added via syringe by mass difference dropwise over 5 min. After 15 min., more nBuLi solution (2.5 M in hexanes, 6.9 mL, 17 mmol) was added, dropwise over 4 min. After stirring at this temperature for 24 h, the reaction mixture was cooled in a dry ice/acetone bath. After stirring for 20 min., diethyl ketomalonate (3.6 mL, 23 mmol) was added to the reaction mixture, dropwise over 8 min. After 5 min., the reaction was quenched by rapid addition of aq. HCl (2.0 M, 12.5 mL), and cooling was ended. The resulting mixture was partitioned between dichloromethane and half-saturated brine. The aqueous layer was extracted once more with dichloromethane, and the combined organic layers were dried (sodium sulfate) and concentrated to a clear, yellow oil (5.45 g). Chromatographic purification (354 g silica gel, heptane to 3:7 EtOAc/heptane gradient) afforded the title compound as a white solid (1.06 g, 53 % yield, ca. 90 % purity). LCMS (ESI) m/z: 375.3[M+Na] (19 %). 1H NMR (400 MHz, CDCl3) delta 1.29 (t, J = 7.1 Hz, 3H), 1.33 (t, J = 7.1 Hz, 3H), 1.35 (s, 9H), 2.48 (d, J = 7.8 Hz, 1H), 4.24 (dq, J = 10.8, 7.1 Hz, 1H), 4.32 (dq, J = 10.8, 7.1 Hz, 1H), 4.34 (dq, J = 10.7, 7.1 Hz, 1H), 4.38 (dq, J = 10.8, 7.1 Hz, 1H), 5.85 (dt, J = 7.8, 0.6 Hz, 1H), 6.64 (dd, J = 8.1, 2.0 Hz, 1H), 6.66 (dt, J = 2.0, 0.5 Hz, 1H), 7.27 (dt, J = 8.2, 0.6 Hz, 1H). 13C NMR (101 MHz, CDCl3) delta 13.9 (1C), 14.1 (1C), 28.8 (3C), 62.7 (1C), 62.7 (1C), 76.1 (1C), 79.3 (1C), 93.6 (1C), 106.4 (1C), 118.2 (1C), 120.2 (1C), 125.3 (1C), 158.6 (1C), 159.3 (1C), 165.3 (1C), 166.4 (1C).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Rocke, Benjamin N.; Conn, Edward L.; Eisenbeis, Shane A.; Ruggeri, Roger B.; Tetrahedron Letters; vol. 53; 41; (2012); p. 5467 – 5470;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 99548-55-7, 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 99548-55-7 as follows.

Methyl 4-bromo-2-methylbenzoate (2.0 g, 8.73 mmol), cyclopropylboronicacid (1.1 g, 13.10 mmol), potassium phosphate (3.7 g, 17.46 mmol), tricyclohexylphosphine (0.245 g, 0.87 mmol) and palladium(II) acetate (0.195 g, 0.87 mmol) were combined in a sealed tube under nitrogen, then toluene (10 mL) and H20 (1 mL) was added in one portion. The reaction mixture was sealed and heated to 120°C for a period of 16 h. The reaction mixture was allowed to cool and diluted with EtOAc and washed with water. The organic extracts were washed with water and brine, dried and concentrated. The crude obtained was purified by column chromatography using 2-5 percent of EtOAc in hexane to afford the titled compound (1.3 g, 81 percent). FontWeight=”Bold” FontSize=”10″ H NMR (400 MHz, DMSO-dg) delta 7.72 (d, J=8.0 Hz, 1H), 7.01-6.97 (m, 2H), 3.78 (s, 3H), 2.50 (s, 3H), 1.92- 1.91 (m, 1H), 1.02-1.00 (m, 2H), 0.75-0.73 (m, 2H); LC/MS: 191 (Mu+1)+

According to the analysis of related databases, 99548-55-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AURIGENE DISCOVERY TECHNOLOGIES LIMITED; BORUAH, Anima; CHITTY VENKATA, Srikanth; HOSAHALLI, Subramanya; PANIGRAHI, Sunil Kumar; WO2014/125408; (2014); A2;,
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Synthetic Route of 1150566-27-0, 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. 1150566-27-0 name is Ethyl 6-chloroimidazo[1,2-b]pyridazine-3-carboxylate, 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 3,3,3-trifluoropropan-1-ol (19.9 mmol) in DMSO was added NaH (19.9 mmol). The mixture was allowed to stir at room temp under inert atmosphere for 1 h. Ethyl 6-chloroimidazo[1,2-b]pyridazine-3-carboxylate (3.0 g, 13.3 mmol) was added and the reaction was warmed to 100 C until coupling was complete. After purification ethyl 6-(3,3,3-trifluoropropoxy)imidazo[1,2-b]pyridazine-3-carboxylate was obtained (1.2 g, 45%). MS (ESI) calcd for C12H12F3N3O3: 303.08

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 6-chloroimidazo[1,2-b]pyridazine-3-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; GlaxoSmithKline LLC; CASAUBON, Rebecca, L.; NARAYAN, Radha; OALMANN, Christopher; VU, Chi, B.; (583 pag.)EP2768509; (2017); B1;,
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. 5335-05-7, name is Chloromethyl benzoate, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H7ClO2

Chloromethyl benzoate (2.87 g, 16.82 mmol) was dissolved in acetonitrile (20 mL) and treated portionwise with sodium iodide (5.04 g, 33.6 mmol). The resulting mixture was stirred at room temperature for 18 hours. The reaction mixture was diluted with water and extracted with ethyl acetate (x 2). The ethyl acetate layers were combined, dried under magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography (Biotage SP4) eluting with a gradient of 0-20 % ethyl acetate and iso-hexane. Product containing fractions were combined and evaporated under reduced pressure to give the title compound as a yellow oil (3.15 g);1 H NMR (400 MHz, CDCI3): delta 8.06-8.03 (2H, m), 7.63-7.59 (1 H, m), 7.49-7.44 (2H, m), 6.16 (2H, s).

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; PROXIMAGEN LIMITED; DINNELL, Kevin; LIGHTFOOT, Andrew; MORTON, Gillian Elizabeth; WO2011/45353; (2011); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 23786-14-3, These common heterocyclic compound, 23786-14-3, name is Methyl 4-methoxyphenylacetate, 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 methyl 2-(4-methoxyphenyl)acetate (10.0 g, 55.49 mmol) in THF (100 mL) at -78 C was added methyl iodide (23.64 g, 166.5 mmol) very slowly. KO?-Bu (18.68 g, 166.5 mmol) was then added portionwise over 30 min and the reaction mixture was stirred at -78 C for 1 h followed by rt for another 1 h. The reaction was quenched by the addition of water (25 mL) and extracted with EtOAc (2 x 250 mL). The organic layer was dried over Na2S04 and concentrated to obtain the title compound (10.46 g, 91%).

The synthetic route of 23786-14-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TEMPERO PHARMACEUTICALS, INC.; BALOGLU, Erkan; BOHNERT, Gary, J.; GHOSH, Shomir; LOBERA, Mercedes; SCHMIDT, Darby, R.; SUNG, Leonard; WO2013/19682; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics