Tag: M.W=200-300

Electric Literature of 116419-94-4, These common heterocyclic compound, 116419-94-4, name is Methyl 4-methyl-3-(trifluoromethyl)benzoate, 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 4-methyl-3-trifluoromethylbenzoic acid (1.71 g, 8.37 mmol) in DMF (20 mL) was added with potassium carbonate (1.39 g, 10.1 mmol) and the reaction mixture was stirred at room temperature for five minutes. Iodomethane (0.78 mL, 12.5 mmol) was added and the reaction mixture stirred at room temperature for 18 hours. The reaction mixture was diluted with ethyl acetate and washed with water and brine (¡Á2). The organic phase was dried over anhydrous magnesium sulfate, filtered and the filtrate evaporated at reduced pressure to afford methyl 4-methyl-3-trifluoromethylbenzoate. The material was dissolved in carbon tetrachloride (10 mL) and treated sequentially with N-bromosuccinimide (2.74 g, 15.4 mmol) and benzoyl peroxide (catalytic) and heated at 80 C. for 18 hours. The mixture was allowed to cool and diluted with water. The mixture was poured through a hydrophobic frit and the solvent evaporated at reduced pressure to afford methyl 4-(dibromomethyl)-3-trifluoromethylbenzoate. The material was dissolved in acetone/ water (25 mL/5 mL) and silver nitrate (2.38 g, 14.0 mmol) added. (0223) The reaction mixture was stirred at room temperature for 72 hours. The suspension was filtered through a pad of celite and the filtrate diluted with ethyl acetate. The solution was washed with water and brine. The organic phase was dried over anhydrous magnesium sulfate, filtered and evaporated. The residue was dissolved acetone/water (25 mL/5 mL) and silver nitrate (2.38 g, 14.0 mmol) added. (0224) The reaction mixture was stirred at room temperature for 24 hours. The suspension was filtered through a pad of celite and the filtrate diluted with ethyl acetate. The solution was washed with water and brine. The organic phase was dried over anhydrous magnesium sulfate, filtered and evaporated. The residue was purified by flash column chromatography (eluent-100% i-hexane to 8:1 i-hexane/ ethyl acetate) to afford the title compound (0.537 g, 33%). (0225) 1H NMR (400 MHz, CDCl3); delta 10.46-10.45 (m, 1H), 8.46 (s, 1H), 8.35 (d, J=8.2 Hz, 1H), 8.20 (d, J=8.2 Hz, 1H), 4.00 (s, 3H).

Statistics shows that Methyl 4-methyl-3-(trifluoromethyl)benzoate is playing an increasingly important role. we look forward to future research findings about 116419-94-4.

Reference:
Patent; CHIESI FARMACEUTICI S.P.A.; RANCATI, Fabio; Rizzi, Andrea; Carzaniga, Laura; Linney, Ian; Knight, Chris; Schmidt, Wolfgang; (120 pag.)US2018/16267; (2018); A1;,
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Electric Literature of 20921-00-0, 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. 20921-00-0 name is 6-Bromochroman-2-one, 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.

[Step b] To a solution of compound 2 (1.02 g, 4.49 mmol) in tetrahydrofuran (10.0 mL) was added 2 M-aqueous sodium hydroxide solution (5.00 mL), and the mixture was stirred at room temperature for 10 hr. The reaction solution was concentrated under reduced pressure to evaporate the organic solvent, water (10.0 mL) and sodium iodide (1.01 g, 6.74 mmol) were added, and the mixture was cooled to -5C. To the reaction solution was added 2% aqueous sodium hypochlorite solution (20.0 mL) over 40 min, and the mixture was stirred at -5C under cooling for 1 hr. To the reaction solution was added 2 M-aqueous hydrochloric acid solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium thiosulfate solution, saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was dissolved in N,N-dimethylformamide (20.0 mL), potassium carbonate (1.86 g, 13.46 mmol) and methyl iodide (0.850 mL, 13.65 mmol) were added, and the mixture was stirred at room temperature overnight. The reaction solution was ice-cooled, 0.1 M-hydrochloric acid (50.0 mL) was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified by silica gel chromatography to give compound 4 (1.48 g, 82.6%). MS(ESI)m/z: 399, 401 (M+1)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6-Bromochroman-2-one, and friends who are interested can also refer to it.

Reference:
Patent; Mitsubishi Tanabe Pharma Corporation; TAKAHASHI, Taichi; UMINO, Akinori; IIJIMA, Daisuke; TAKAMATSU, Hisayuki; (173 pag.)EP3135667; (2017); 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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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 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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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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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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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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Application 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 suspension of [2- (4-METHYLSULFANYL-PHENYLSULFANYL) ETHYLAMINE HYDROCHLORIDE] salt (0.63 g, 2.69 [MMOLS)] in anhydrous tetrahydrofuran (20 ml) was added triethylamine (0.78 ml, 5.64 mmols) at [0C] under nitrogen. The mixture was stirred for 30 mins. To this was added dropwise a solution of [TERT-BUTYL] bromo acetate (0.42 [ML,] 2.82 [MMOLS)] in anhydrous tetrahydrofuran (10 [ML).] The mixture was warmed to room temperature and stirred fro 18 hours. The solvent was removed under reduced pressure and the residue partitioned between water (50 ml) and diethyl ether (30 [ML).] The aqueous was extracted with diethyl ether (2 x 30 [ML),] the combined organics dried over magnesium sulfate, filtered and the solvent removed under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with a solvent gradient of heptane: ethyl acetate (1: 1) to give the title compound (0.25 g, 29 %) as a colourless oil. [‘H-NMR] (400 MHz, CD30D) : [A] = 1.44 (s, 9H), 2.45 (s, 3H), 2.75 (t, 2H), 3.01 (t, 2H), 3.20 (brs, 2H), 7.20 (d, 2H), 7.33 (d, 2H). LRMS [(ELECTROSPRAY)] : m/z [M + [H] + 314.] Microanalysis : Found: C, 57.28 ; H, 7.38 ; N, 4.41. [C15H23NO2S2] requires C, 57.47 ; H, 7.39 ; N, 4.47%.

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

Reference:
Patent; PFIZER LIMITED; PFIZER INC.; WO2004/16583; (2004); A1;,
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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. 148547-19-7, name is Methyl 4-bromo-3-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 148547-19-7

2l2′-dimethyl-1 l1 ‘-biphenyl-4-carboxylic acidStep 1: methyl 2,2′-dimethyl-1, 1’-biphenyl-4-carboxylate To a solution of methyl 4-bromo-3-methylbenzoate (ABCR, 15 g, 65 mmol) in toluene (200 mL) and water (200 mL), was added o-tolylboronic acid (10.68 g, 78 mmol) followed by potassium carbonate (45.25 g, 32.7 mmol) and tetrakis(triphenylphosphine)palladium(0) (3.78 g, 3.3 mmol). The mixture was degassed with N2 and refluxed at 120 C for 6 hours. After the completion of reaction, the reaction mixture was cooled to RT. The organic phase was separated and evaporated under reduced pressure. The crude compound was passed through a silica column using hexane as eluent to get the title compound as a white solid (15 g, 95%). 1H NMR (DMSO-d6, 400 MHz) delta 7.91 (s, 1 H), 7.83-7.81 (m, 1 H), 7.33-7.30 (m, 2H), 7.28-7.26 (m, 1 H), 7.25-7.22 (m, 1 H), 7.07-7.05 (m, 1 H), 3.86-3.81 (s, 3H), 2.09-2 (s, 3H), 1.97-1.92 (s, 3H). HPLC (Method B), Rt: 3.01 min (purity: 98.71 %).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 148547-19-7.

Reference:
Patent; MERCK SERONO S.A.; MUZERELLE, Mathilde; QUATTROPANI, Anna; MONTAGNE, Cyril; DORBAIS, Jerome; WO2010/69949; (2010); A1;,
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