Month: January 2021

These common heterocyclic compound, 619-42-1, name is Methyl 4-bromobenzoate, 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. Computed Properties of C8H7BrO2

To a stirred solution of methyl 4-bromobenzoic acid methyl ester (45 g, 209.0 mmol) in MeOH (500 mL), hydrazine hydrate (39.31 g, 627.0 mmol) was added at RT and heated to 65 C for 12h. After cooling the reaction mixture to RT, the solvent was removed under reduced pressure. The residue was slurred with diethyl ether (300 mL). The solid was filtered off and dried under suction to afford the title compound as an off white solid (40 g, 93% yield). NMR (400 MHz, DMSO-d6) delta 9.84 (s, 1H), 7.76- 7.73 (m, 2H), 7.66-7.64 (m, 2H), 4.49 (s, 2H) 1H NMR (DMSO-d6, 400MHz) delta 9.84 (s, 1H), 7.76-7.73 (m, 2H), 7.66-7.63 (m, 2H), 4.42 (b, 2H). LC/MS (Method A): 217.0(M+H)+. HPLC (Method F) Rt 2.02 min (Purity: 99.6%).

The synthetic route of Methyl 4-bromobenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARES TRADING S.A.; QUATTROPANI, Anna; SWINNEN, Dominique; WO2013/182274; (2013); A1;,
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Application of 1186-73-8, 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 1186-73-8 as follows.

Step 13; methyl 10-(((tert-butyldimethylsilyl)oxy)methyl)-l-(2,4-dimethoxybenzyl)-4- hydroxy-9-methyl-2-oxo-2,5,6,9-tetrahydro-lH-pyrido[2′,3′:4,5]oxepino[3,2- f] indole-3-carboxylate A solution of N-(8-((tert-butyldimethylsilyloxy)methyl)-9-methyl-3,4-dihydro-2H- oxepino[3,2-f]indol-5(9H)-ylidene)-l-(2,4-dimethoxyphenyl)methanamine (3.81 g crude) and trimethyl methanetricarboxylate (2.9 g, 15.0 mmol) in Ph20 (15 mL) was heated at 230 C for 15 min. The reaction mixture was cooled to room temperature and purified on silica gel using EtO Ac/Hex (0-60% gradient) to afford the product (2.0 g, 43%) as a yellow foam. XH NMR (500 MHz, DMSO-i) delta ppm 0.00 (d, J=0.95 Hz, 6 H) 0.77 – 0.83 (m, 9 H) 1.87 – 1.96 (m, 2 H) 2.88 – 2.96 (m, 1 H) 3.48 (s, 3 H) 3.64 (d, J=1.89 Hz, 6 H) 3.77 (s, 3 H) 4.21 (br. s., 2 H) 4.74 (s, 2 H) 4.98 – 5.07 (m, 1 H) 6.24 (s, 1 H) 6.37 (s, 2 H) 6.61 – 6.68 (m, 1 H) 7.21 (s, 1 H) 7.31 – 7.40 (m, 1 H) 13.28 – 13.36 (m, 1 H). LC-MS: 633.2 [M-H]”, RT 1.80 min.

According to the analysis of related databases, 1186-73-8, 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; WO2013/33228; (2013); A1;,
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Synthetic Route 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.

b) Fluoro[(phenylmethoxy)methyl]propanedioic acid, diethyl ester In a 500 ml. flask, sodium hydride (4.08 g., 102 mmole, 60% dispersion in mineral oil) was suspended in dry tetrahydrofuran (100 ml.). The suspension was cooled to -20C., and benzyl chloromethyl ether (18.6 ml., 134 mmole) was added via syringe. To the resulting mixture was added a solution of diethyl fluoromalonate (12 g., 67.4 mmole) in dry tetrahydrofuran (300 ml.) via addition funnel (rinsed with 5 ml. of solvent). The mixture was warmed to 0C. and stirred for 3 hours. Then, the mixture was warmed to room temperature and stirred for 1.5 hours. The mixture was cooled to 0C. and quenched with dry ethanol (20 ml.). The reaction solution was stirred at room temperature for 30 minutes, and then slowly poured into saturated ammonium chloride (300 ml.) at 0C. The mixture was diluted with diethyl ether (300 ml.) and separated. The aqueous layer was further extracted with diethyl ether (2 x 100 ml.), and the combined organic layers were washed with saturated aqueous sodium bicarbonate (2 x 100 ml.). The organic layer was dried over sodium sulfate, filtered, and the solvent was removed by rotary evaporation to afford 31 g. of a brown oil. Flash chromatography (16 – 20% ethyl acetate-hexane) afforded 18.8 g. of the title compound.

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

Reference:
Patent; E.R. SQUIBB & SONS, INC.; EP554025; (1993); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 50995-48-7,Some common heterocyclic compound, 50995-48-7, name is Methyl 2,5-dibromopentanoate, molecular formula is C6H10Br2O2, 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.

Reference Example 1 To a solution of 3.06 g of 2-amino-4,5-dimethylthiophenol in 50 ml of dimethylformamide was added 5.48 g of methyl 2,5-dibromovalerate at room temperature with stirring. The mixture was stirred for 14 hours, poured into water, and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4), and concentrated. The residue was washed with a mixture of ether and hexane to obtain 4.35 g (69.3percent) of 2-(3-bromopropyl)-6,7-dimethyl-2H-1,4-benzothiazin-3(4H)-one as crystals. Recrystallization from methanol gave prisms, m.p. 151¡ã-153¡ã C. IR(Nujol)cm-1: 3200, 1660. NMR delta(ppm)in CDCl3: 1.37-2.27(4H, m), 2.42(6H, s), 3.23-3.4(1H, m), 3.37(2H, t, J=6 Hz), 6.64(1H, s), 7.03(1H, s), 8.9(1H, broad). Elemental Analysis for C13 H16 BrNOS, Calcd.: C 49.69; H 5.13; N 4.46, Found: C 49.84; H 4.97; N 4.75.

The synthetic route of 50995-48-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Chemical Industries, Ltd.; US4640916; (1987); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 379228-57-6, A common heterocyclic compound, 379228-57-6, name is Methyl 2-amino-4,6-difluorobenzoate, molecular formula is C8H7F2NO2, 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-amino-4,6-difluorobenzoate (3 g, 16.0 mmol, 1.0 eq) in DMSO (5 mL) was added cyclopentanamine (2.73 g, 32.0 mmol, 2.0 eq) and the mixture was heated at 80 C. overnight. The mixture was cooled to RT, diluted with water (5 mL) and extracted with DCM (40 mL*2). The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography (Petroleum ether:DCM, 40:1, v/v to Petroleum ether:EtOAc, 30:1 to 20:1, v/v) to afford the title compound (863 mg, 21%) as a red solid. LCMS: [M+H]+ 253.1.

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; Ribon Therapeutics Inc.; Schenkel, Laurie B.; Vasbinder, Melissa Marie; Kuntz, Kevin Wayne; Swinger, Kerren Kalai; (179 pag.)US2019/194174; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 35450-36-3, 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. 35450-36-3, name is Methyl 2-bromo-5-methoxybenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

a) 2-[(E)-2-(3-Chlorophenyl)vinyl]-5-methoxybenzoic acid methyl ester To a stirred solution of 2-bromo-5-methoxybenzoic acid methyl ester (17.7 g, 72.2 mmol) and 3-chlorovinylbenzene (9.17 mL, 72.2 mmol) in anhydrous acetonitrile (180 mL) was added triethylamine (20.10 mL, 144 mmol) and tris(o-tolyl)phosphine (2.85 g, 9.38 mmol). The reaction mixture was sparged with argon for 5 min, palladium(II) acetate (1.62 g, 7.22 mmol) was added and the mixture heated at 85 C. under an argon atmosphere for 21 h. The product mixture was filtered through celite, concentrated in vacuo, the residue dissolved in ethyl acetate (400 mL) and washed with 1 N HCl (aq.) (200 mL) and brine (200 mL). The combined aqueous layers were back-extracted with ethyl acetate (200 mL). The ethyl acetate extracts were combined, dried (MgSO4) and concentrated under reduced pressure to give the crude 2-[(E)-2-(3-chlorophenyl)vinyl]-5-methoxybenzoic acid methyl ester as a red-brown, viscous oil which was used in the next step without further purification. Data for 2-[(E)-2-(3-chlorophenyl)vinyl]-5-methoxybenzoic acid methyl ester: 1H NMR (300 MHz, CDCl3): delta 7.91 (d, 1H), 7.63 (d, 1H), 7.49 (dd, 1H), 7.44 (d, 1H), 7.41 (ddd, 1H), 7.26 (d, 1H), 7.21 (ddd, 1H), 7.08 (dd, 1H), 6.83 (d, 1H), 3.94 (s, 3H), 3.86 (s, 3H) ppm.

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 2-bromo-5-methoxybenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; N.V. Organon; US2008/64678; (2008); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 927-68-4, name is 2-Bromoethyl acetate, 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 927-68-4, name: 2-Bromoethyl acetate

After dissolving ethyl imidazole-2-carboxylate (200 mg, 1.43 mmol) in 5 ml of N,N-dimethylformamide and adding cesium carbonate (931 mg, 2.85 mmol) for 0.5 h,Add 2-bromoethyl acetate (385mg, 2.14mmol), warm to 80 for 2h, complete the reaction by TLC, stop the reaction, cool to room temperature, dilute with water,Extract with ethyl acetate (3¡Á20 ml), combine the organic layers, wash with saturated brine, dry over anhydrous sodium sulfate, filter and concentrate to obtain crude product.Purified by column chromatography (PE: EA=3: 1) to give a pale yellow liquid, ie compound1-(2-acetoxyethyl)-1H-imidazole-2-carboxylic acid ethyl ester 26b (300 mg, yield 92.8%).

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; Sichuan University; Li Guobo; Wang Zhenling; (36 pag.)CN111253317; (2020); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 35450-36-3, name is Methyl 2-bromo-5-methoxybenzoate, 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 35450-36-3, Recommanded Product: 35450-36-3

Intermediate 11 :Methyl 2-bromo-5-methoxy benzoate (20.0 g, 81.61 mmol), tri methyl bo roxine (13.36 ml_, 97.93 mmol), Pd(dppf)CI2 (1.0 g, 1.36 mmol), dioxane (350 ml_), water (50 ml_), and Cs2CO3 (22.5 g, 163 mmol) were stirred at 11OC (oil bath) under nitrogen for 16 hours. After cooling, the solid was removed by filtration. The solution was concentrated and purified by SGC (10:1 EtOAc/hexanes) to give 11 (12.1 g, 80%). Mass calculated for formula C10H12NO3 , 180.20, observed LCMS m/z 181.20 (M+H).NMR (H1); 2.35(3H,CH3) 3.73(3H, – OCH3),3.88(3 H, CO2-CH3),6.86-7.5(m,3H,Aromatic)

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; SCHERING CORPORATION; WO2009/14637; (2009); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 144267-96-9, A common heterocyclic compound, 144267-96-9, name is Ethyl 3,4-difluorobenzoate, molecular formula is C9H8F2O2, 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 the respective phenol and the benzoate derivative or, respectively, the carboxylic acid derivative of an aromatic 6-membered heterocycle having 1 or 2 N-atoms, as defined in connection with formula (I), or their substituted derivatives in an appropriate solvent, preferably a polar aprotic solvent, most preferably DMSO, and preferably under addition of anhydrous K2C03 , was stirred at a temperature between 80C and 120C depending on the substrate until the limiting reactant was fully converted. The reaction was guenched by addition of water, extracted with organic solvent (preferably Et20, EtOAc and DCM depending on the substrate). The combined organic layers were washed with sat. agueous NaCI solution, dried over Na2S04 and evaporated to dryness under reduced pressure. The crude product was purified by flash column chromatography to give the desired biarylether. (V138) General procedure A: Ethyl 3,4-difluorobenzoate (348 mg, 1.87 mmol, 1.00 eguiv), 4-(tert- butyOphenol (336 mg, 2.24 mmol, 1.20 eguiv) and K2C03 (388 mg, 2.80 mmol, 1.50 eguiv) in DMSO (2 ml_) were stirred at 100 C for 22 h. Purification by column chromatography (EtOAc/petroleum ether 1/40) gave the desired product as colourless oil (451 mg, 1.43 mmol, 76%); HRMS (ESI) m/z calcd. for C19H2203F+ [M+H]+ 317.1547, found: 317.1549; NMR (400 MHz, Chloroform-cO delta 7.85 (dd, J = 11.2, 2.0 Hz, 1H), 7.80 – 7.73 (m, 1H), 7.42 – 7.35 (m, 2H), 7.02 – 6.94 (m, 3H), 4.37 (q, J = 7.1 Hz, 2H), 1.39 (t, J = 7.1 Hz, 3H), 1.33 (s, 9H).

The synthetic route of 144267-96-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ECOLE POLYTECHNIQUE FEDERALE DE LAUSANNE (EPFL); REINMUELLER, Viktoria; ZHU, Jieping; (56 pag.)WO2017/158190; (2017); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 23426-63-3, name is Methyl 2-bromo-2-methylpropanoate, This compound has unique chemical properties. The synthetic route is as follows., Formula: C5H9BrO2

Step B; 2,5-Dimethyl-4-thiocyanato-phenol 72 (5.75 g, 32.1 mmol) is dissolved in acetonitrile (25 mL). Powdered cesium carbonate (15.32 g, 47.0 mmol) is added. Then 2- bromo-2-methyl-propionic acid methyl ester (4.50 mL, 34.8 mmol) is added and the mixture is stirred at 6O0C for 18 h. Filtration and concentration, followed by silica gel chromatography (0-50% ethyl acetate in hexanes) yielded 2-(2,5-dimethyl-4-thiocyanato- phenoxy)-2-methyl-propionic acid methyl ester 73 as an oil: 1H-NMR (400 MHz, CDCb) (rotamers are present; the data given is for the most abundant isomer) delta = 7.39 (s, IH), 6.50 (s, IH), 3.78 (s, 3H), 2.42 (s, 3H), 2.20 (s, 3H), 1.62 (s, 6H). MS calcd. for Ci4HnNNaO3S (MH-Na+) 302.1 , found 302.1.

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 23426-63-3.

Reference:
Patent; IRM LLC; WO2007/56497; (2007); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics