Month: January 2021

Related Products of 685-88-1, These common heterocyclic compound, 685-88-1, name is Diethyl fluoromalonate, 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 diethyl 2 fluoromalonate ester (1.0 g, 5.617 mmol) was added ethanol (10 ml), water (10ml), and lithium hydroxide monohydrate (0.943 g, 22.47mmol), then the reaction was stirred well for 16h at 50C. Then the reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was diluted in MTBE and water, then mixture was acidify with 6N HCl and then extracted with MTBE (5 x 50 ml). The combined organic layer were dried over Na2SO4, filtered and concentrated under reduced pressure to give 400 mg (yield 58%) of a white solid corresponding to 2-fluoromalonic acid. The crude product used in the next step without further purification. Synthesis of 2,4-dichloro-3-fluoroquinoline, intermediate 348-I-2

The synthetic route of 685-88-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GENOSCIENCE PHARMA; BRUN, Sonia; BERET, Antoine; BASSISSI, Firas; HALFON, Philippe; COURCAMBECK, Jerome; (275 pag.)WO2017/191599; (2017); A1;,
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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. 792-74-5, name is Dimethyl [1,1′-biphenyl]-4,4′-dicarboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: 792-74-5

General procedure: To a solution of benzo[b]thiophene (8) (2.15g, 16.0mmol) in 20ml dry THF under an argon atmosphere at?30¡ãC, n-BuLi (10.0ml, 16.0mmol, 1.6M n-hexane) was added slowly. The mixture was treated with the corresponding ester and stirred at room temperature. After quenching with saturated aqueous NH4Cl-solution, the residue was extracted with CHCl3. The organic phase was dried (Na2SO4) and the solvent evaporated.

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; Katzsch, Felix; Gruber, Tobias; Weber, Edwin; Journal of Molecular Structure; vol. 1114; (2016); p. 48 – 64;,
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Electric Literature of 252881-74-6, 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 252881-74-6 as follows.

Synthesis of tert-Butyl 1 -((3 S,4aS,6aR,6b S,8aS, 11S,1 2aR, 1 4aR, 1 4b S)- 11 -((benzyloxy)carbonyl)-4,4,6a,6b,8a,11,14b-heptamethyl-14-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,1 4a, 1 4b-icosahydropicen-3 -yl)- 1 -oxo-5, 8,11 -trioxa-2-azatetradecan- 1 4-oate (110-1). Into a250-mL round-bottom flask, was placed 1-7 (515 mg, 0.85 mmol, 1.00 equiv), DCM (50 mL), tert-butyl 3-2-[2-(2-aminoethoxy)ethoxy]ethoxypropanoate (589 mg, 2.12 mmol, 2.50 equiv), TEA (0.885 mL, 7.50 equiv). The resulting solution was stirred overnight at room temperature. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with EtOAc/petroleum ether (1:1). This resulted in 533 mg (74%) of 110-1 as a lightyellow solid.

According to the analysis of related databases, 252881-74-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARDELYX, INC.; LUEHR, Gary; DRAGOLI, Dean; LEADBETTER, Michael; CHEN, Tao; LEWIS, Jason; (181 pag.)WO2019/60051; (2019); A1;,
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Adding a certain compound to certain chemical reactions, such as: 431-47-0, name is Methyl 2,2,2-trifluoroacetate, 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 431-47-0, Application In Synthesis of Methyl 2,2,2-trifluoroacetate

N-benzyl p-toluenesulfonamide (100 mg, 0.38 mmol), DMF (4 mL), potassium t-butoxide (129 mg, 1.15 mmol, 3 eq.) was added to the reaction flask in turn, and stirred at room temperature for 5 minutes. After the potassium tert-butoxide was uniformly dispersed, methyl trifluoroacetate (0.15 mL, 1.52 mmol, 4 eq.) was slowly injected into the reaction flask, and after 10 hours of reaction, stirring was stopped. It was extracted twice with ethyl acetate and distilled water, and then washed with a saturated NaCI solution. The magnesium sulfate was removed by filtration, and the solvent was evaporated. Purification by column chromatography to give N-methyl-N-benzyl-p-toluenesulfonamide (104 mg, yield 100%)

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:
Patent; Guangdong Petrochemical College; Xiao Duoduo; Zheng Xin; Zeng Jiechun; Huang Jiawei; Zhou Rujin; Guan Ying; Liang Jieling; (8 pag.)CN109369506; (2019); A;,
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Reference of 33155-58-7, A common heterocyclic compound, 33155-58-7, name is tert-Butyl 2-(4-Bromophenyl)acetate, molecular formula is C12H15BrO2, 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 an N?-purged flask containing the title compound from the previous step (1.55 g, 5.55 mmol), were added PdCl2(PPh3)2 (584 mg, 0.83 mmol), w-BuOH (30 mL), and DIEA (5.00 mL, 27.8 mmol). The mixture was placed under an atmosphere of carbon monoxide and stirred vigorously at 110 0C. After 1 h, the reaction mixture was allowed to cool to room temperature, and was concentrated in vacuo. Purification by silica gel chromatography (0 to 100% EtOAc in hexanes) provided the title compound: LCMS (ESI): m/z 237.3 [M – tBu]+; 1H NMR (500 MHz, CDCl3): delta 7.99 (d, J = 8.0 Hz, 2 H)5 7.34 (d, J = 8.0 Hz, 2 H), 4.32 (t, J = 6.5 Hz, 2 H), 1.77-1.72 (m, 2 H), 1.51-1.45 (m, 2 H), 1.43 (s, 9 H), 0.98 (t, J = 8.0 Hz, 3 H).

The synthetic route of 33155-58-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; WO2007/136577; (2007); A2;,
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Synthetic Route of 136333-97-6, A common heterocyclic compound, 136333-97-6, name is Methyl 4-(2-bromoethyl)benzoate, molecular formula is C10H11BrO2, 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.

[0487] Scheme 3 , Step I: Preparation of (i?)-methyl 4-(2-(5 -(((tert- butyldimethylsilyl)oxy)methyl)-3 ,3 -difluoro-2-oxopyrrolidin- 1 -yl)ethyl)benzoate (lib; PG=TBS) [0488] To a suspension consisting of sodium hydride (60% in mineral oil, 61 mg, 1.5 mmol) and sodium iodide (251 mg, 1.67 mmol) in DMF (40 mL) was added dropwise a solution consisting of (i?)-5-(((tert-butyldimethylsilyl)oxy)methyl)-3,3-difluoropyrrolidin-2- one (intermediate 9; PG=TBS, 370 mg, 1.39 mmol) in DMF (5 mL). The mixture was stirred at room temperature for two hours followed by 50C for 30 minutes. To the reaction mixture was added dropwise methyl 4-(2-bromoethyl)benzoate (406 mg, 1.67 mmol) in DMF (5 mL), and stirring continued overnight at 50C. The mixture was diluted with ethyl acetate and washed sequentially with 0.5 N hydrochloric acid, a 5% aqueous solution of sodium thiosulfate, 50% brine, and brine. The organic phase was dried over sodium sulfate, filtered, and concentrated. The residue was purified by silica gel chromatography. Elution with ethyl acetate :heptane (increasing solvent strength, 1 :50 v/v to 1 : 10 v/v) followed by eluting with methanol-dichloromethane (1 :50 v/v) afforded the title intermediate (39 mg, 6.6%); TLC R/ 0.6 (solvent system: 70:30 v/v heptane:ethyl acetate); -NMR (CDC13) delta 7.9 (d, 2H), 7.28 (d, 2H), 3.98-3.91 (m, 1H), 3.9 (s, 3H), 3.74-3.48 (m, 2H), 3.46-3.35 (m, 2H), 3.1-2.9 (m, 2H), 2.48-2.18 (m, 2H), 0.8 (s, 9H), 0.0 (s, 6H); MS (ESf ) m/z 445.1 (M+NH3). [0489] Significant improvement of the yield (in relation to (R)-5-(((tert- butyldimethylsilyl)oxy)methyl)-3,3-difluoropyrrolidin-2-one) was realized by repeated additions of sodium hydride and methyl 4-(2-bromoethyl)benzoate to the reaction mixture.

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; CAYMAN CHEMICAL COMPANY, INC.; MYOMETRICS, LLC; BARRETT, Stephen, Douglas; CISKE, Fred, Lawrence; COLOMBO, Joseph, Michael; ENDRES, Gregory, William; GERMAIN, Bradlee, David; KORNILOV, Andriy; KRAMER, James, Bernard; UZIEBLO, Adam; OWEN, Thomas, Allen; O’MALLEY, James, Paul; WO2014/15246; (2014); A1;,
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Synthetic Route of 121-98-2,Some common heterocyclic compound, 121-98-2, name is Methyl 4-methoxybenzoate, molecular formula is C9H10O3, 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 solution of methyl 4-tert-butylbenzoate (5.15 g, 26.8 mmol) and hydrazine monohydrate (1.50 ml, 30.0 mmol) in MeOH (15 mL) was stirred for 2 d. After the removal of the solvent in vacuo, the residue was recrystallized from MeOH to give 4-tert-butylbenzohydrazide (1b) (2.94 g, 15.3 mmol, 57%) as a colorless crystal. 1 H-NMR (300 MHz, DMSO-d 6 ): delta 9.68 (s, 1H), 7.75 (d, J = 8.5 Hz, 2H), 7.45 (d, J = 8.5 Hz, 2H), 4.44 (s, 2H), 1.28 (s, 9H) ppm.

The synthetic route of 121-98-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sakurai, Masayoshi; Kawakami, Rina; Kihara, Nobuhiro; Tetrahedron Letters; (2019);,
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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. 17100-63-9, name is Methyl 4-bromo-3-methoxybenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of Methyl 4-bromo-3-methoxybenzoate

To a stirred solution of methyl 4-bromo-3-methoxybenzoate (11.2 g) in THF (130 mL), methanol (45 mL) and water (45 mL) was added a 1 M solution of lithium hydroxide in water (140 mL). The mixture was stirred at room temperature for 1 h. The solvent was removed in vacuum. Water was added and I N hydrochloric acid was added with ice bath cooling until pH 4 was reached. The precipitated solid was collected by filtration, washed with waterand dried in vacuum to give 10.1 g of the title compound, that was used without further purification.1H-NMR (300MHz, DMSO-d6): a [ppm] = 3.87 (5, 3H), 7.42 (dd, 1H), 7.50 (d, 1H),7.68 (d, 1H), 13.21 (br. s., 1H).

The synthetic route of 17100-63-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; SCHULZE, Volker; SCHIROK, Hartmut; KOSEMUND, Dirk; BRIEM, Hans; BADER, Benjamin; BOeMER, Ulf; WENGNER, Antje Margret; SIEMEISTER, Gerhard; LIENAU, Philip; STOeCKIGT, Detlef; LUeCKING, Ulrich; SCHALL, Andreas; WO2014/198594; (2014); A1;,
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Synthetic Route of 54535-22-7, 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 54535-22-7 as follows.

[0217] A l L three-necked flask fitted with a mechanical stirrer was charged with 2- phenylaminomethylene-malonic acid diethyl ester (26.3 g, 0.100 mol), polyphosphoric acid (270 g) and phosphoryl chloride (750 g). The mixture was heated to 70 0C and stirred for 4 h. The mixture was cooled to room temperature and filtered. The residue was treated with aqueous Na2CO3 solution, filtered, washed with water and dried. 4-Hydroxyquinoline-3- carboxylic acid ethyl ester was obtained as a pale brown solid (15.2 g, 70%). The crude product was used in next step without further purification.

According to the analysis of related databases, 54535-22-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VERTEX PHARMACEUTICALS, INC.; WO2007/79139; (2007); A2;,
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Reference of 4341-76-8, These common heterocyclic compound, 4341-76-8, name is Ethyl 2-butynoate, 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.

Example 31 Synthesis of tert-Butyl(2-methylpyrazolo[1,5-a]pyridin-3-yl)carbamate (CE298) Step 1: 1-Aminopyridinium iodide (10 g), ethyl but-2-ynoate (6.05 g), potassium carbonate (7.45 g) were mixed in anhydrous DMF (50 mL). The reaction mixture was stirred at ambient temperature for 3 days. A mixture of water (100 mL), ethyl acetate (100 mL) and hexane (100 mL) was added and the product was collected by filtration. The filter cake was washed with a mixture of ethyl acetate_hexane=1:1, affording 6.4 g of ethyl 2-methylpyrazolo[1,5-a]pyridine-3-carboxylate (70% yield).

Statistics shows that Ethyl 2-butynoate is playing an increasingly important role. we look forward to future research findings about 4341-76-8.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; Wang, Shaomeng; Zhao, Yujun; Zhou, Bing; Aguilar, Angelo; Liu, Liu; Bai, Longchuan; McEachern, Donna; Sun, Duxin; Wen, Bo; Luo, Ruijuan; Zhao, Ting; Chinnaiyan, Arul; Asangani, Irfan A.; Stuckey, Jeanne; Meagher, Jennifer Lynn; Ran, Xu; US2015/246923; (2015); A1;,
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