Tag: M.W=200-300

Application of 25542-62-5, 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. 25542-62-5, name is Ethyl 6-bromohexanoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

The compound represented by Formula 8-a was synthesized by Reaction 8-1.Ethyl 2-methylacetatoacetate (23.5 g, 163 mmol) and ethyl 6-bromohexanoate (40.0 g, 179 mmol) were stirred in 200 ml of ethanol and liquid sodium ethoxide was added dropwise thereto. The mixture was stirred at 80 C. for 10 h. After completion of the reaction, the solid was filtered off. The filtrate was distilled under reduced pressure and extracted with dichloromethane and a 2 N aqueous solution of hydrochloric acid. The organic layer was treated with anhydrous sodium sulfate and distilled under reduced pressure (47.7 g). After removal of the solvent, 300 ml of water was added, followed by stirring under reflux for 10 h. After completion of the reaction, the reaction solution was extracted with dichloromethane, treated with sodium sulfate, and distilled under reduced pressure (25 g, 71%).1H NMR (400 MHz, CDCl3): delta=10.85 (1H, s), 2.52 (1H, m), 2.36 (2H, m) 2.30 (3H, s), 1.65 (4H, m), 1.35 (4H, m), 1.09 (3H, d)

The synthetic route of Ethyl 6-bromohexanoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SFC CO., LTD.; Song, Ju-man; Min, Seon-Gi; Lee, Seung-Soo; Lee, Do-min; Park, Kyung-Hwa; Hwang, Moon-Chan; Shin, Bong-Ki; Je, Jong-Tae; (72 pag.)US10473666; (2019); B2;,
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6274-50-6, name is Methyl 2-(4-methoxyphenyl)-2-methylpropanoate, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Product Details of 6274-50-6

To a solution of methyl 2-(4-methoxyphenyl)acetate (10.0 g, 48.00 mmol) in MeOH (20 mL) was added dropwise a solution of NaOH (7.69 g, 192.3 mmol) in water (50 mL). The reaction mixture was stirred at rt for 6 h. The MeOH was distilled off at reduced pressure and water (25 mL) was added. The aqueous layer was washed with Et20 and then acidified to pH=4 using 6.0 M HC1. The resultant precipitate was filtered, washed with hexanes, and dried. The resultant solid was dissolved in CH2CI2 (150 mL) and cooled to -78 C followed by the addition of BBr3 (1.0 M solution in CH2C12) (72.0 mL, 72.00 mmol) over 30 min. After the completion of the addition, the temperature was raised to 0 C, and the reaction mixture was stirred for an additional 30 min. Water was slowly added and the organic layer was separated, dried over Na2S04; and concentrated to provide the title compound (4.30 g, 50%). lU NMR (400 MHz, DMSO-d6) delta ppm 12.17 (br s, 1H), 9.31 (s, 1H), 7.14 (d, 2H), 6.71 (d, 2H), 1.42 (s, 6H).

The synthetic route of 6274-50-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TEMPERO PHARMACEUTICALS, INC.; BALOGLU, Erkan; BOHNERT, Gary, J.; GHOSH, Shomir; LOBERA, Mercedes; SCHMIDT, Darby, R.; SUNG, Leonard; WO2013/19682; (2013); A1;,
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Related Products of 1186-73-8, These common heterocyclic compound, 1186-73-8, name is Trimethyl methanetricarboxylate, 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.

Step 1: Methyl 10-chloro-l-(2,4-dimethoxybenzyl)-4-hydroxy-2-oxo-2,5,6,7-tetrahydro-lH-benzo[6,7]cyclohepta[l,2-b]pyridine-3-carboxylate The crude imine was combined with diphenyl ether (5 mL) and trimethylmethanetricarboxylate (1.07 g, 5.63 mmol). The reaction was stirred in a pre-heated 190 C bath for 1 hr. After cooling to room temperature, the mixture was purified by silica gel chromatography (5-50% EtOAc in hexanes). Trituration with acetone yielded the title compound (620 mg, 49%) as an off-white solid. 1H NMR (acetone- d6): delta 1.45 (m, 1H), 1.85-2.05 (m, 2H), 2.26 (m, 1H), 2.53 (dd, J = 13 Hz, 6 Hz, 1H), 2.96 (dd, J = 14 Hz, 6 Hz, 1H), 3.61 (s, 3H), 3.75 (s, 3H), 3.94 (s, 3H), 5.05 (d, J = 16 Hz, 1H), 5.28 (d, J = 16 Hz, 1H), 6.41 (m, 2H), 6.81 (d, J = 8.5 Hz, 1H), 7.27 (d, J = 8.5 Hz, 1H), 7.37 (m, 1H), 7.41 (dd, J = 8 Hz, 2.5 Hz, 1H), 13.83 (s, 1H)

The synthetic route of 1186-73-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PTC THERAPEUTICS, INC.; GERASYUTO, Aleksey, Igorevich; ARNOLD, Michael, A.; CHEN, Guangming; KARP, Gary, Mitchell; QI, Hongyan; TURPOFF, Anthony, A.; WANG, Jiashi; WOLL, Matthew, G.; ZHANG, Nanjing; ZHANG, Xiaoyan; BRANSTROM, Arthur, A.; NARASIMHAN, Jana; DUMBLE, Melissa, L.; HEDRICK, Jean; WEETALL, Marla, L.; (229 pag.)WO2016/25932; (2016); 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. 99548-55-7, name is Methyl 4-bromo-2-methylbenzoate, A new synthetic method of this compound is introduced below., Computed Properties of C9H9BrO2

To a solution of NBS (38.8 g, 218 mmol) and methyl 4-bromo-2-methylbenzoate (50.0 g, 218 mmol) in CC14 (1.00 L) was added AIBN (3.58 g, 21.8 mmol) and the solution was stirred for 16 hours at reflux. The reaction was cooled to ambient temperature, quenched by addition of water (300 mL), and the organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica chromatography, eluting with hexanes: ethyl acetate (100: 1) to afford the title compound as a solid. 1H NMR (300 MHz, CDCI3) delta 7.81 (d, / = 8.4 Hz, 1H), 7.63 (m, 1H), 7.51 (d, / = 8.4 Hz, 1H), 4.90 (s, 2H), 3.94 (s, 3H).

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; MERCK SHARP & DOHME CORP.; CHILDERS, Matthew Lloyd; FULLER, Peter; GUERIN, David; KATZ, Jason David; PU, Qinglin; SCOTT, Mark E.; THOMPSON, Christopher F.; MARTINEZ, Michelle; FALCONE, Danielle; TORRES, Luis; DENG, Yongqi; KURUKLASURIYA, Ravi; ZENG, Hongbo; BAI, Yunfeng; KONG, Norman; LIU, Yumei; ZHENG, Zhixiang; WO2014/146491; (2014); A1;,
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Reference of 3650-78-0, 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. 3650-78-0, name is Methyl 3-(4-bromophenyl)acrylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(R)-3-oxo hexahydroimidazo[1,5-a]pyrazine-7(1H)-carboxylic acid tert-butyl ester (1.80 g, 7.46 mmol),Methyl 4-bromocinnamate (2.0 g, 8.3 mmol),Palladium acetate (84 mg, 0.37 mmol),2-di-tert-butylphosphino-2′,4′,6′-triisopropylbiphenyl (320 mg, 0.75 mmol) andCesium carbonate (3.65g, 11.2mmol)Soluble in 1,4-dioxane (20 mL),The reaction was stirred at 100 C for 12 h under a nitrogen atmosphere.Cool to room temperature, filter, filter cake washed with dichloromethane (100 mL),The residue was purified by silica gel column chromatography (PE/EA (V/V)=3/1).The title compound was obtained as a white solid (1.95 g, 65.1%).

The synthetic route of Methyl 3-(4-bromophenyl)acrylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Liu Xinchang; Ren Qingyun; Yan Guanghua; S ·geerdeman; Zhang Yingjun; (200 pag.)CN109678859; (2019); A;,
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Some common heterocyclic compound, 36076-26-3, name is Diethyl 2,2-(1,4-phenylene)diacetate, molecular formula is C14H18O4, 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. COA of Formula: C14H18O4

1-1 Ethyl 2-nitrobenzene-1,4-diacetate A solution of ethyl benzene-1,4-diacetate (CAS Reg. No. 36076-26-3) (14.0 g; 55.937 mmol) prepared in accordance with JP-A 57-183740 in conc. sulfuric acid (28 ml) was cooled with ethanol/dry ice, and 90% nitric acid (4.0 g; 57.134 mmol) was added dropwise thereto at -5 to 10 C. After 10 min., the reaction solution was added dropwise to a solution of ethyl acetate (140 ml) in ice-water (140 ml). Then, the organic layer was separated and washed with water, a saturated aqueous sodium bicarbonate and brine, followed by adding anhydrous magnesium sulfate and activated charcoal thereto. After filtering, the solvent was removed, to give the title compound (yield: 16.16 g, 54.726 mmol, 97.8%). m.p.: 50-51 C.; 1H-NMR(400 MHz, CDCl3) delta (ppm); 1.27 (3H, t, J=7.1 Hz) 1.28 (3H, t, J=7.1 Hz), 3.70 (2H, s), 4.00 (2H, s), 4.17 (2H, q, J=7.1 Hz), 4.18 (2H, q, J=7.1 Hz), 7.32 (1H,d, J=7.9 Hz), 7.53 (1H, dd, J=7.9, 1.5 Hz), 8.05 (1H, d, J=1.5 Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 36076-26-3, its application will become more common.

Reference:
Patent; Eisai Co., Ltd.; US6573384; (2003); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 756525-95-8, name is tert-Butyl 9-Amino-4,7-dioxanonanoate, 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 756525-95-8, Recommanded Product: 756525-95-8

[00584] To a 0.14M solution of carboxylic acid (1.0 equiv) in DCM was added HATU (1.5 equiv) and DIPEA (3.0 equiv). The mixture was stirred for 1 h, then amino-PEG-ester (1.0 equiv) was added. The reaction was allowed to stir until consumption of carboxylic acid, as indicated by LCMS. The mixture was poured into H2O and the aqueous phase was extracted with DCM. The combined organic phases were washed with brine, dried with anhydrous Na2S04, filtered and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography to afford the product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl 9-Amino-4,7-dioxanonanoate, and friends who are interested can also refer to it.

Reference:
Patent; REVOLUTION MEDICINES, INC.; SEMKO, Christopher; PITZEN, Jennifer; WANG, Gang; TIBREWAL, Nidhi; AGGEN, James Bradley; THOTTUMKARA, Arun P.; BURNETT, G. Leslie; GLIEDT, Micah James Evans; KISS, Gert; WON, Walter; LEE, Julie Chu-li; GILL, Adrian Liam; (538 pag.)WO2018/204416; (2018); 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. 55666-43-8, name is tert-Butyl 3-bromopropanoate, A new synthetic method of this compound is introduced below., Safety of tert-Butyl 3-bromopropanoate

NaH (25.1 mg, 60%, 0.63 mmol) and then tert-butyl 3-bromopropanoate (69.7 uL, 0.42 mmoL) was added to 5-morpholino-3-(quinolin-3-yl)pyrazolo[l,5-a]pyrimidin-7- amine (72.3 mg, 0.21 mmoL) in DMF (3 mL). The mixture was stirred at room temperature until LCMS indicated complete conversion. The reaction mixture was diluted with Sat. NH4C1 and then extracted with ethyl acetate (x2). The combined organic layers were washed with brine and dried with Na2SC»4. Evaporation of solvent afforded the crude tert-butyl 3-(5- morpholino-3-(quinoIin-3-yl)pyrazolo[l,5-a]pyrimidin-7-ylamino)propanoate. The crude ester was heated with 4N HC1 (4 mL) and 1, 4-dioxane (4 mL) at 50C for 3h. Concentration provided 3-(5-morpholino-3-(quinolin-3-yl)pyrazolo[lf5-a]pyrimidin-7-ylamino)propanoic acid. LCMS tR = 1.30 Min (5 min run, UV 2s4nm)- Mass calculated for, M+ 18.1, observed LC/MS m/z 419.2 (M+H).

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; SCHERING CORPORATION; MENG, Zhaoyang; REDDY, Panduranga Adulla, P.; SIDDIQUI, M. Arshad; MANDAL, Amit, K.; LIU, Duan; ZHAO, Lianyun; MCRINER, Andrew; WO2012/27234; (2012); A1;,
Ester – Wikipedia,
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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. 54810-63-8, name is Methyl 2-chloro-5-methoxybenzoate, A new synthetic method of this compound is introduced below., Computed Properties of C9H9ClO3

At -10C to -5C in anhydrous THF (200 mL)Methyl 2-chloro-5-methoxybenzoate EEE-1 (4.55 g, 22.7 mmol)LiAlH4 (1.72 g, 45.4 mmol) was added portionwise to the solution.Increase the temperature to 0 C. After addition, the reaction was stirred at 0 C for 2 hours.The reaction mixture was quenched with 5% NaOH.The reaction mixture was filtered through a pad of Celite. Add THF to the diatomaceous earth block(100 mL) and EtOAc (100 mL) and stir at 25 C for 0.5 h.The mixture was filtered and the combined organic layers were dried over Na2SO4 and concentrated to provide crude EEE-2 (4.5 g) as a colorless oil and used directly in the next step.

The synthetic route of 54810-63-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; KUMPF, ROBERT ARNOLD; MCALPINE, INDRAWAN JAMES; MCTIGUE, MICHELE ANN; PATMAN, RYAN; RUI, EUGENE YUANJIN; TATLOCK, JOHN HOWARD; TRAN-DUBE, MICHELLE BICH; WYTHES, MARTIN JAMES; (445 pag.)TW2018/2074; (2018); A;,
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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. 653-92-9, name is Methyl 2-bromo-4-fluorobenzoate, A new synthetic method of this compound is introduced below., Safety of Methyl 2-bromo-4-fluorobenzoate

EXAMPLE 18AMETHYL 4-FLUORO-2-PHENETHYLBENZOATEMethyl 2-bromo-4-fluorobenzoate (1.00 g), (E)-styrylboronic acid (0.89 g), tetrakis(triphenylphosphine)palladium(0) (0.50 g), and K3PO4 (2.28 g) were stirred in dioxane (17 mL) at 90 C. for 24 hours. The reaction mixture was chromatographed on silica gel with 1-5% ethyl acetate/hexanes. The product in methanol (10 ml) was added to 20 wt % of fresh dry 5% Pd-C and stirred 4 days with H2 in a pressure bottle. The mixture was filtered through a nylon membrane and concentrated.

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; ABBOTT LABORATORIES; US2010/184750; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics