Esters-buliding-blocks

These common heterocyclic compound, 59247-47-1, name is tert-Butyl 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. SDS of cas: 59247-47-1

4-[4-(4-carboxyphenyl)-piperazin-1-yl]-benzoic acid tert-butyl ester To a degassed mixture of 4-(piperazin-1-yl)-benzoic acid ethyl ester (1.45g, 6.2 mmol), 4-bromobenzoic acid tert-butyl ester (1.75g, 6.8 mmol), cesium carbonate (3.9g, 12 mmol) in dioxane (25 mL) was added tris(dibenzylideneacetone)dipalladium (300 mg, 5 molpercent) and 2-(dicyclohexylphosphino)-2′,4′,6′-tris(isopropyl)-biphenyl (x-phos, 300 mg, 10 molpercent). The mixture was heated in a sealed tube with stirring at 100 ¡ãC for 3 hrs. Solvents were evaporated and the residue was extracted with ethyl acetate and water. The organic layer was dried over sodium sulfate and solvents were evaporated. The crude material was purified through a flash column chromatography using ethyl acetate and hexanes to give the intermediate 4-[4-(4-ethoxycarbonylphenyl)-piperazin-1-yl]-benzoic acid tert-butyl ester as solid (1.3 g, 51 percent yield) The above intermediate, (1.2g, 2.68 mmol) was suspended in methanol (100 mL) and THF (100 mL) and sodium hydroxide solution (1N, 80 mL) was added. The mixture was refluxed for 2 hrs and then concentrated. The mixture was acidified with 1N HCl and the solid formed was filtered to give 4-[4-(4-carboxyphenyl)-piperazin-1-yl]-benzoic acid tert-butyl ester (1.1g). LCMS calcd for C22H26N204 (m/e) 382. Obsd: 381 (M-H+)

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

Reference:
Patent; Madrigal Pharmaceuticals, Inc.; BOLIN, David, R.; CHEUNG, Adrian, Wai-hing; HAMILTON, Matthew, Michael; MARCOPULOUS, Nicholas; McDERMOTT, Lee, Apostle; QIAN, Yimin; EP2350311; (2013); B1;,
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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. 52727-57-8, name is Methyl 2-amino-5-bromobenzoate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 52727-57-8

To a suspension of lithium aluminium hydride (0.33 g, 8.7 mmol) in THF (10 ml) was added a solution of methyl 2-amino-5-bromobenzoate (2.0 g, 8.7 mmol) in 20 ml THF at 0 0C under nitrogen. Then stirring was continued for 2 h. 0.64 ml water, 2 M solution of sodium hydroxide (0.64 ml) and again 1.28 ml water were added before the resulting mixture was filtered through celite. Evaporation of the solvent and purification of the crude product by flash chromatography on silica gel (dichloromethane/ethyl acetate, 2/1) yielded (2-amino-5- bromophenyl)methanol (1.0 g, 5.2 mmol, 59 %) as off-white solid.

According to the analysis of related databases, 52727-57-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UNIVERSITAeT SAARLANDES; WO2009/135651; (2009); A1;,
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Adding a certain compound to certain chemical reactions, such as: 609-12-1, name is Ethyl 2-bromo-3-methylbutanoate, 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 609-12-1, Recommanded Product: 609-12-1

To a solution (50 mL) of ethyl 3-fluoro-4-(1H-pyrazol-1-yl)phenol (2.0 g) and 2-bromo-3-methylbutanoate (2.4 mL) in dimethylformamide was added potassium carbonate (2.33 g), and the mixture was stirred at 80C for 24 hr. The reaction mixture was added to water, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (2.47 g). MS (API+): [M+H]+ 307.1.

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, Ethyl 2-bromo-3-methylbutanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Takeda Pharmaceutical Company Limited; NAKAMURA, Shinji; MIKAMI, Satoshi; KAWASAKI, Masanori; NOMURA, Izumi; ASHIZAWA, Tomoko; TANIGUCHI, Takahiko; EP2873669; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 50413-30-4, name is Methyl 2-amino-4-methoxylbenzoate, 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 50413-30-4, Quality Control of Methyl 2-amino-4-methoxylbenzoate

Methyl 2-amino-4-(methyloxy) benzoate (3.78 g, 20.86 mmol) was dissolved in 25 mL of water, 15 mL of ethanol and 2.2 mL of concentrated HCl. A solution of ICl (1.1 mL, 21.9 mmol) in 3.8 mL concentrated HCl and 14 mL of water at 5 C was added to the aniline solution. The reaction was stirred overnight and was then filtered to obtain 6.9 g of a light brown solid. MS: m/z: 308 [M+H]+

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-amino-4-methoxylbenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GlaxoSmithKline Intellectual Property Development Limited; BURY, Michael, Jonathan; CASILLAS, Linda, N.; CHARNLEY, Adam, Kenneth; DEMARTINO, Michael, P.; DONG, Xiaoyang; EIDAM, Patrick, M.; HAILE, Pamela, A.; MARQUIS, Robert, W., Jr.; RAMANJULU, Joshi, M.; ROMANO, Joseph, J.; SINGHAUS, Robert, R., Jr.; SHAH, Ami, Lakdawala; WANG, Gren; (82 pag.)EP2744501; (2016); B1;,
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Electric Literature of 1128-00-3, A common heterocyclic compound, 1128-00-3, name is Ethyl 2-aminocyclohex-1-enecarboxylate, molecular formula is C9H15NO2, 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 ethyl 2-aminocyclohex-1-enecarboxylate (33) (3.33 g, 19.7 mmol) and pyridine (2.33 g, 29.5 mmol) in dry THF (50 ml) at -5 C slowly within 1 h 2-bromoacetyl bromide (3.93 g, 19.5 mmol) was added. The reaction mixture was stirred at the same temperature for 45 min. and partitioned between ethyl acetate (50 ml) and satd NaHCO3 (50 ml). The water phase was extracted with ethyl acetate (3 ¡Á 30 ml). The organic extracts were combined, and successively washed with satd NaHCO3 solution (50 ml), water (2 ¡Á 50 ml), satd NaCl solution (50 ml), and dried (Na2SO4). The solvent was evaporated, the residue was mixed with ethyl acetate (50 ml), and the solid material was filtered off. The filtrate was evaporated to dryness and the residue was dried in vacuo over P2O5 to give 5.00 g (88%) of compound 34 as a brown oil, which was immediately utilized in the next step. 1H NMR (CDCl3) delta: 1.30 (t, J = 7.1 Hz, 3H), 1.55-1.68 (m, 4H), 2.30-2.36 (m, 2H), 2.90-2.96 (m, 2H), 3.86 (s, 2H), 4.21 (q, J = 7.1 Hz, 2H), 12.08 (br s, 1H). GCMS m/z: 289.0 M+.

The synthetic route of 1128-00-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bobileva, Olga; Bokaldere, Rasma; Gailite, Vija; Kaula, Ilze; Ikaunieks, Martins; Duburs, Gunars; Petrovska, Ramona; Mandrika, Ilona; Klovins, Janis; Loza, Einars; Bioorganic and Medicinal Chemistry; vol. 22; 14; (2014); p. 3654 – 3669;,
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Application of 17100-65-1,Some common heterocyclic compound, 17100-65-1, name is Methyl 2-bromo-4-methoxybenzoate, molecular formula is C9H9BrO3, 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.

(0580) Methyl 2-bromo-4-methoxybenzoate (20 g, 0.082 mol) was dissolved in N,N-dimethylformamide (100 mL), and cuprous cyanide (10.95 g, 0.123 mol) was added. (0581) The reaction was carried out at 150 C. for 4 h. The mixture was cooled, and was poured into saturated ammonium chloride aqueous solution. The mixture was extracted with ethyl acetate (150 mL¡Á3). The organic phases were combined, dried with anhydrous sodium sulfate, filtrated, and concentrated. The crude product was purified by silica gel column chromatography (petroleum ether:ethyl acetate=5:1) to get the title compound (9.8 g, yield: 62%).

The synthetic route of 17100-65-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Xuanzhu Pharma Co., Ltd.; WU, Frank; (117 pag.)US2017/112833; (2017); A1;,
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Synthetic Route of 15963-40-3,Some common heterocyclic compound, 15963-40-3, name is Methyl 3-methylenecyclobutanecarboxylate, molecular formula is C7H10O2, 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 3-methylenecyclobutanecarboxylate (5.3 g, 42.4 mmol, 1.0 eq) in THF (30 mL) was added BH3 (12.6 mL, 12.6 mmol, 0.3 eq, 1 M) dropwise at 0 C. Then the reaction mixture was warmed to ft and stirred for 4 h. MeOH (15 mL) was added and the mixture was stirred for 30 mm at 0 C. NaOH (4.2 mL, 3M) and H202 (1.4 g, 42.4 mmol, 1.0 eq) wereadded and stirred at 0 C for 1 h. The mixture was quenched with water (30 mL) and extracted with Et20 (60 mL X 2). The combined organic phases were dried over Na2SO4 After filtration and concentration, 3.3 g of methyl 3-(hydroxymethyl)cyclobutanecarboxylate as yellow oil was obtained. Y: 54%. ESI-MS (M+H): 145.0. ?H NMR (400 MHz, CD3OD) (5: 3.69 (s, 1.3H), 3.67 (s, 1.7H), 3.59 (s, 0.4H), 3.58 (s, 0.5H), 3.50 (s, 0.4H), 3.48 (s, 0.5H), 3.12-3.03 (m, 1H), 2.48-2.38 (m, 1H), 2.35-2.22 (m, 2H), 2.08-1.94 (m, 2H).

The synthetic route of 15963-40-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOGEN MA INC.; CHAN, Timothy; GUCKIAN, Kevin; JENKINS, Tracy; THOMAS, Jermaine; VESSELS, Jeffery; KUMARAVEL, Gnanasambandam; MEISSNER, Robert; LYSSIKATOS, Joseph, P.; LUCAS, Brian; LEAF, Irina; DUFFIELD, Jeremy; GENUNG, Nathan; (113 pag.)WO2017/127430; (2017); A1;,
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Synthetic Route of 7270-63-5, 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. 7270-63-5 name is 5-Diazo-2,2-dimethyl-1,3-dioxane-4,6-dione, 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.

General procedure: 1- (3,4,5-trimethoxyphenyl) hexan-1-one (3aa) (53.3 mg, 0.2 mmol, 100 mol%),[IrCp * Cl 2] 2 (3.2 mg, 0.004 mmol, 2 mol%) or[RhCp * Cl 2] 2 (2.5 mg, 0.004 mmol, 2 mol%),AgNTf2 (6.2 mg, 0.016 mmol, 8 mol%),AgOAc (2.6 mg, 0.016 mmol, 8 mol%) andIn an oven-dried sealed tube filled with 5-diazo-2,2-dimethyl-1,3-dioxane-4,6-dione (4a) (40.8 mg, 0.24 mmol, 120 mol%), EtOH (18.4 mg, 0.4 mmol, 200 mol%) and DCE (1 mL) were added in air at room temperature.The reaction mixture was stirred at 60 C for 20 h. The reaction mixture was cooled to rt, diluted with EtOAc (3 mL) and concentrated in vacuo. The residue was purified by flash column chromatography (n-hexane / EtOAc = 12: 1) to give 5aa (50.2 mg, 71%) as a yellow solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Diazo-2,2-dimethyl-1,3-dioxane-4,6-dione, and friends who are interested can also refer to it.

Reference:
Patent; SUNGKYUNKWAN University Research & Business Foundation; Kim In-su; Kim Hyeong-sik; (40 pag.)KR2019/87836; (2019); A;,
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Reference of 42122-75-8, These common heterocyclic compound, 42122-75-8, name is Methyl 5-amino-2-chlorobenzoate, 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.

General procedure: To a solution 15 (490 mg, 1.0 eq, 0.92 mmol) in CH2Cl2 (50 mL) was added HATU (525 mg, 1.5 eq, 1.38 mmol), 4-methylmorpholine (0.30 mL, 3.0 eq, 2.8 mmol) and methyl 3-aminobenzoate hydrochloride (208 mg, 1.2 eq, 1.1 mmol). The reaction mixture was stirred at room temperature overnight. After the solvent was concentrated in vacuo, the residue was purified by chromatography (petroleum ether/acetone = 3/1) to afford compound 16 as white solid (360 mg, 59%).

Statistics shows that Methyl 5-amino-2-chlorobenzoate is playing an increasingly important role. we look forward to future research findings about 42122-75-8.

Reference:
Article; Chen, Yue-Ting; Tang, Chun-Lan; Ma, Wei-Ping; Gao, Li-Xin; Wei, Yi; Zhang, Wei; Li, Jing-Ya; Li, Jia; Nan, Fa-Jun; European Journal of Medicinal Chemistry; vol. 69; (2013); p. 399 – 412;,
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Synthetic Route of 2178-24-7,Some common heterocyclic compound, 2178-24-7, name is Ethyl (2-bromophenyl)acetate, molecular formula is C10H11BrO2, 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 1(4′-Methylbiphenyl-2-yl)acetic acid a) Ethyl (4′-methylbiphenyl-2-yl)acetateTo a mixture composed of 243.1 mg (1 mmol) of ethyl 2-(2-bromophenyl)- acetate, 3.7 ml of toluene, 57.8 mg (0.05 mmol) of tetrakis(triphenylphosphine)- palladium and 127.2 mg (1.2 mmol) of anhydrous sodium carbonate are added EPO 169.9 mg (1.25 mmol) of 4-methy.phenylboronic acid, followed by addition of 2.21 ml (0.055 mmol) of methanol. The reaction medium is heated at 85C for 16 hours with stirring. After cooling, 10 ml of water and 8 ml of ethyl acetate are added with stirring, and the mixture is then filtered through a fluted filter paper. The organic phase is recovered and the aqueous phase is extracted again with ethyl acetate.The combined organic phases are washed with water (2 x 10 ml), dried over Na2SO4 and then concentrated to give 310 mg of oil, which is purified by flash chromatography on a column of silica, in a dichloromethane/heptane mixture (1 :1). 201 mg of a colourless oil are obtained.Yield: 79%NMR (CDCI3): 1.2 (t, J=7.2 Hz, 3H); 2.5 (s, 3H); 3.7 (m, 2H), 4.1 (q, J=7.2 Hz, 2H); 7.3 (m, 8H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl (2-bromophenyl)acetate, its application will become more common.

Reference:
Patent; MERCK PATENT GMBH; WO2006/58592; (2006); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics