Tag: M.W=200-300

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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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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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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Related Products of 49851-36-7,Some common heterocyclic compound, 49851-36-7, name is Methyl 2-(2-aminophenyl)acetate hydrochloride, molecular formula is C9H12ClNO2, 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.

TEA (0.324 mL, 2.325 mmol) was added to a mixture of 3-acetamido-5-bromobenzoic acid (CAS 78238-1 1 -6) (200 mg, 0.775 mmol) and HATU (324 mg, 0.852 mmol) in DMF (3 mL) at 23 C. After 5 min, methyl 2-(2-aminophenyl)acetate hydrochloride (CAS 49851 -36-7) (165 mg, 0.775 mmol) was added and the resulting mixture was stirred at room temperature overnight. The mixture was partitioned between 4: 1 EtOAc/heptanes and water. The aqueous layer was extracted with 4: 1 EtOAc/heptanes. The combined organic layers were washed with 5% aqueous LiCI solution, the organics were dried (Na2S04), filtered and concentrated. The residue was purified by silica gel chromatography (EtOAc/heptanes 20-80%) to provide the title compound. MS (ESI+) m/z 405.2, 407.2 (M+H).

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

Reference:
Patent; NOVARTIS AG; BELANGER, David B.; FLOHR, Stefanie; GELIN, Christine Fang; JENDZA, Keith; JI, Nan; LIU, Donglei; LORTHIOIS, Edwige Liliane Jeanne; KARKI, Rajeshri Ganesh; MAINOLFI, Nello; POWERS, James J.; RANDL, Stefan Andreas; ROGEL, Olivier; VULPETTI, Anna; YOON, Taeyoung; WO2015/9977; (2015); 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. 39149-80-9, name is tert-Butyl 2-bromopropanoate, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C7H13BrO2

A.i. (RS)-tert-Butyl 2-(methylsulfonyl)propanoate : To a suspension of sodium methanesulfinate (100 g; 929 mmol) in tBuOH (350 mL) was added iert-butyl-2-bromopropionate (150 mL; 877 mmol). The reaction mixture was stirred at 90C for 24 h under nitrogen atmosphere, then cooled to rt and concentrated to dryness. The residue was partitioned between water (750 mL) and EA (600 mL). The aq. layer was extracted with EA (2 x 500 mL). The evaporation residue afforded the title compound as a white yellow solid (175 g; 96% yield). 1H NMR (DMSO-d6) delta: 4.24 (q, J = 7.2 Hz, 1H); 3.1 1 (s, 3H); 1.45 (s, 9H); 1.40 (d, J = 7.2 Hz, 3H).

According to the analysis of related databases, 39149-80-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; IDORSIA PHARMACEUTICALS LTD; DIETHELM, Stefan; GAUVIN, Jean-Christophe; JACOB, Loic; PANCHAUD, Philippe; SCHMITT, Christine; SURIVET, Jean-Philippe; TIDTEN-LUKSCH, Naomi; (79 pag.)WO2019/86452; (2019); A1;,
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Reference of 10203-58-4,Some common heterocyclic compound, 10203-58-4, name is Diethyl isobutylmalonate, molecular formula is C11H20O4, 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) 2-(S-Acetylthiomethyl)4-methylpentanoic acid Hydrolysis of 91.1 g of isobutyldiethyl malonate is accomplished by digesting a solution of the ester in 300 ml of methanol and 400 ml of 10% NaOH for 6 hours at 80 C. The solution is concentrated in vacuo to 400 ml. It is acidified with 10% aqueous HCl and product is extracted with ethyl acetate to yield 67.6 g of the diacid. This crystallized on standing. M.P. 94-95 C. The diacid is suspended in 400 ml of water and cooled to 5 C. Aqueous 40% dimethylamine (50 g) and aqueous 37% formaldehyde (35.7 g) are added in that order. The solution is stirred overnight and Mannich base solid product is filtered and dried in vacuo to yield 57.3 g. M.P. 134-137 C. with CO2 and dimethylamine given off. The Mannich base (57.3 g) is suspended in 200 ml of water and 43 g of 50% NaOH in 100 ml of water is added until pH is 9. This solution is heated on the steam cone under nitrogen overnight. It is neutralized with 10% HCl and product is extracted with ethyl acetate to yield 23.8 g. The crude unsaturated acid is chromatographed (twice) on 200 g of silica to give 21.6 g of pure acid.

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

Reference:
Patent; E. R. Squibb & Sons, Inc.; US4382081; (1983); A;,
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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. 46064-79-3, name is Methyl 3-amino-4-bromobenzoate, This compound has unique chemical properties. The synthetic route is as follows., category: esters-buliding-blocks

A mixture of methyl 2-oxocyclooctanecarboxylate (32.0 g, 174 mmol), methyl 3-amino-4-bromobenzoate (20.0 g, 87 mmol) and ethanol (120 mL) was heated to reflux, at an oil bath of 130 C, acetic acid (1.5 mL) was added and the mixture was reflux for 1.5 hours. Hot PPA (200 g, 120 C) was added to the reaction mixture carefully. The reaction mixture was heated at an oil bath of 130 C for 3 hours. After cooling for a while, ice (200 g), ethyl acetate (60 mL) and petroleum ether (60 mL) were added to the reaction mixture, the mixture was concentrated until 200 mL solvent was removed. Then water (600 mL) and ethyl acetate (60 mL) were added, the resulting mixture was stayed at room temperature overnight. A light brown solid was slowly formed. The mixture was filtered and the filtered cake was dried to give a light brown solid, which was placed into methanol (90 mL). SOCl2 (30 mL) was added dropwise with cooling with an ice-bath. The resulting mixture was heated to reflux for 4 hours, concentrated and treated with saturated NaHCO3 solution (60 mL) and ethyl acetate (30 mL), filtered and the filtered cake was dried to give desired product (6.6 g) as a pale white solid (21%).

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 46064-79-3.

Reference:
Patent; BEIGENE, LTD.; ZHOU, Changyou; REN, Bo; WANG, Hexiang; WO2013/97226; (2013); A1;,
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Related Products of 706791-83-5,Some common heterocyclic compound, 706791-83-5, name is Methyl 3-amino-5-bromobenzoate, molecular formula is C8H8BrNO2, 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 7 mL vial was added a carboxylic acid compound (332 mg, 1.2 mmol), methyl 3-amino-5-bromobenzoate (270 mg, 1.2 eq)EDCI (3.0 eq), HOBt (3.0 eq) and DIPEA (3.0 eq) were dissolved in DMF (0.3 M) and stirred at room temperature for 16 hRespectively. After completion of the reaction, the mixture was extracted three times with a mixed solvent of H2O / EA, and the organic layer was washed with saturated sodium carbonate. The organic layerAfter drying with MgSO4, the solvent was concentrated under reduced pressure, and a silica gel column was carried out to obtain the title compound (475 mg, 83%)

The synthetic route of 706791-83-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; YONSEI University Office of Research Affairs / University Industry Foundation; Korea Research Institute of Chemical Technology; Jang Seong-yeon; Lee Hyeok; Kim Seong-hwan; Kim Beom-tae; Kim Seong-su; Huh Jeong-nyeong; Im Hwan-jeong; Im Seung-gil; Kang Myeong-mo; Noh Gyeong-tae; Lee Gyeong-ro; Choi Ji-won; (147 pag.)KR2017/94087; (2017); A;,
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Synthetic Route of 6279-86-3, 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 6279-86-3 as follows.

Put 300 ml methylbenzene and 60% sodium hydride 3.3g (0.0825 mol) into the 500 ml four-neck flask with reflux condenser pipe, dropping pipette, stirrer and thermometric instrument which is protected by dry nitrogen; and then add 19.3g (0.083 mol) methane tricarboxylic acid triethyl ester into the flask at the temperature of below 80C and protected for 2h by heat preservation; add 33.3g (0.075 mol) bromine sulfonium salts into the flask and then raise the temperature and control the temperature of the entire flask at 80C for a 15h reaction; cool it to the normal temperature and use 5% sulfuric acid to adjust the pH to pH=3; separate the organic layer and extract the water layer by 100 ml methylbenzene for two times; use 40 ml 5% sodium bicarbonate water solution wash the organic layer for two times; dry the oil layer by anhydrous sodium sulfate, filtrate and reduce pressure to recycle faint yellow fluid, finally get the target object-2.5g tri-ester dibenzyl biotin (95.5% of the theoretical value), and the HPLC measured content is 97.8% with no impurity 5 (hereinafter to be referred as dicarboxylic ester)

According to the analysis of related databases, 6279-86-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Zhejiang Medicine Co., Ltd.; EP2433942; (2012); 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. 29263-94-3, name is Diethyl 2-bromo-2-methylmalonate, A new synthetic method of this compound is introduced below., category: esters-buliding-blocks

General procedure: To a 7 mL vial equipped with magnetic stir bar was added bromomalonate (1.0 equiv,0.40 mmol), 2,6-lutidine (1.0 equiv, 0.40 mmol), tris[2-phenylpyridinato-C2,N]iridium(III) (1 mol %, 4.0 mumol), and heterocycle (5.0 equiv, 2.0 mmol). Dryacetonitrile or DMA (0.5 mL, 0.8 M) was then added and the reaction was sparged withN2 for 15 min. The reaction was set to stir under nitrogen at room temperature surroundedby a string of 1W or two strings of 4W blue LEDs for 24 h. The reaction mixture wasthen diluted with ethyl acetate and extracted with water. The aqueous layer was extractedwith ethyl acetate (2 x 10 mL). The combined organic layers were washed with brine,dried over Na2SO4, and concentrated in vacuo. The residue was purified bychromatography on silica gel, using the solvent system indicated.

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; Swift, Elizabeth C.; Williams, Theresa M.; Stephenson, Corey R. J.; Synlett; vol. 27; 5; (2016); p. 754 – 758;,
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