Tag: M.W=200-300

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. 915213-54-6, name is Ethyl 2-(4,4-difluorocyclohexyl)acetate, A new synthetic method of this compound is introduced below., Computed Properties of C10H16F2O2

To a solution ofethyl 2-(4-oxocyclohexyl)acetate(0.4 g) inDCM(5 mL) was addedDeoxo-Fluor(0.881 mL) andEtOH(0.038 mL). The reaction mixture was stirred at rt for 16 h and then diluted with sat. NaHCO3and EtOAc. The organic phase was washed with water, sat. NaCl and dried over anhydrous Na2SO4, filtered and dried to yield ethyl 2-(4,4-difluorocyclohexyl)acetate (0.4 g). To a solution ofethyl 2-(4,4-difluorocyclohexyl) acetateinTHF/MeOH(2 mL) was added 1NNaOH(1 mL), and the reaction mixture was stirred at rt for 16 h. The reaction mixture was concentrated, then diluted with EtOAc and acidified with 1N HCl. The organic phase was washed with sat. NaCl, dried over anhydrous Na2SO4, filtered and concentrated to yield2-(4,4-difluorocyclohexyl)acetic acidas ayellowsolid.1H NMR (400 MHz, DMSO-d6) ppm 12.13 (1H, br. s.), 2.06-2.28 (3H, m), 1.92-2.03 (1H, m), 1.72-1.91 (4H, m), 1.31-1.48 (1H, m), 1.10-1.31 (2H, m).

The synthetic route of 915213-54-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hewawasam, Piyasena; Lopez, Omar D.; Tu, Yong; Wang, Alan Xiangdong; Xu, Ningning; Kadow, John F.; Meanwell, Nicholas A.; Gupta, Samayamuthula Venkata Satya Arun Kumar; Kumar, Indasi J. Gopi; Ponugupati, Suresh Kumar; Belema, Makonen; US2015/23913; (2015); 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. 55099-31-5, name is Ethyl 10-bromodecanoate, A new synthetic method of this compound is introduced below., SDS of cas: 55099-31-5

1f. Preparation of Compound 6 A 3-neck 300 mL round-bottomed flask equipped with a reflux condenser, magnetic stir bar and a nitrogen inlet was charged with 4 g (1 equivalent) of 2-hydroxybenzonitrile, absolute ethanol 140 mL, and 12.54 mL (1 equivalent) of sodium ethoxide. This mixture was stirred at 25 C. for 15 minutes. Ethyl 10-bromodecanoate (9.4 g, 1 equiv.) was then added dropwise over 10 minutes. The resulting mixture was heated to reflux (75 C.) for 72 hours. The reaction mixture was cooled and the solids filtered off. The solvent was removed on a rotary evaporator. The crude residue was dissolved in ethyl acetate (300 mL) and washed with 1/2 saturated NaHCO3 (2*100 mL), H2O (1*100 mL) and brine (1*50 mL). The organic layer was dried to give 10 g of the crude ester. The crude material was then dissolved in ethanol (100 mL) and water (20 mL). LiOH (3.3 g) was added and the resulting mixture was heated to reflux (75 C.) for 3 hours. The solution was cooled and the solvent removed. 20 mL of H2O was added and the aqueous solution was acidified to a pH of about 3 with concentrated HCl. The solution was transferred to a 4 C. refrigerator to cool. A tan colored solid began to precipitate. This material was collected by vacuum filtration and dried on the high vacuum overnight to give the crude acid. These solids were further purified by recrystallization from ethyl acetate/hexanes (95/5) to give 7.1 g of the product, 10-(2-cyanophenoxy)decanoic acid (78% yield). Melting point: 82-84 C. Molecular Formula with water: C17H23NO3*0.0532. Combustion analysis: %C: 70.33 (calc’d), 69.82 (found); %H: 8.02(calc’d), 7.89(found); %N: 4.82 (calc’d), 4.82 (found).

The synthetic route of 55099-31-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Moye-Sherman, Destardi; Gschneidner, David; US2003/199427; (2003); A1;,
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Adding a certain compound to certain chemical reactions, such as: 31273-66-2, name is Ethyl 2,3-dichlorobenzoate, 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 31273-66-2, Safety of Ethyl 2,3-dichlorobenzoate

General procedure: A mixture of substituted ethyl benzoate (12a-g) (0.1M) and hydrazine hydrate (0.3M) was heated under reflux for 30min. Ethanol (20mL) was added to the refluxing mixture as a solvent in order to homogenize the solution, the resulting mixture was further allowed for 6h. Excess of ethanol was distilled out and the content was allowed to cool. The crystals formed were filtered and washed thoroughly with water and dried.

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Reference:
Article; Rakse, Monika; Karthikeyan, Chandrabose; Deora, Girdhar Singh; Moorthy; Rathore, Vandana; Rawat, Arun K.; Srivastava; Trivedi, Piyush; European Journal of Medicinal Chemistry; vol. 70; (2013); p. 469 – 476;,
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19063-56-0, name is 7-Bromo-2H-chromen-2-one, 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. name: 7-Bromo-2H-chromen-2-one

General procedure: A 10 mL vial equipped with a small magnetic stirring bar wascharged with the appropriate bromo O-hetarene (1.0 equiv, 100mg), Pd(OAc)2 (5 mol%), and CuI (1.0 equiv). Anhyd DMF (1 mL)and the appropriate 1,3-azole (2.0 equiv) were added, and thevessel was purged with N2 and sealed with a PEEK snap cap. Themixture was stirred for 5 min at r.t. before the vessel was placedin the microwave reactor and the mixture was heated to 140 Cwith stirring for the appropriate time (usually 1 h). The solutionwas then cooled to r.t., diluted with EtOAc (15 mL), washed withsat. aq NH4Cl (2 × 15 mL) and dilute aq Na2S2O3 (10 mL). Theaqueous phases were extracted with EtOAc (2 × 10 mL), and theorganic phases were combined and washed with sat. aq NH4Cl(10 mL) and brine. Some H2O was added if any solids precipitatedduring the extraction. The combined organic phases weredried (MgSO4), filtered, and concentrated. The residue was purifiedby column chromatography (silica gel).

The synthetic route of 19063-56-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sipos, Zoltan; Konya, Krisztina; Synlett; vol. 29; 18; (2018); p. 2412 – 2416;,
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Application of 76308-26-4, A common heterocyclic compound, 76308-26-4, name is Ethyl 2-(trans-4-aminocyclohexyl)acetate hydrochloride, molecular formula is C10H20ClNO2, 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 cyclohexyl-[5-fluoro-2-((_R)-methoxy-phenyl-methyl)-benzoimidazol-l- yl] -acetic acid (350 mg, 0.88 mmol, 1.0 equiv) in DMF (5 mL) was added triethylamine (179 mg, 240 muL, 1.77 mmol, 2.0 equiv) and HATU (403 mg, 1.06 mmol, 1.2 equiv) and the mixture stirred at 40 0C. After 15 min, trans- (4-amino-cyclohexyl) -acetic acid ethyl ester hydrochloride (235 mg, 1.06 mmol, 1.2 equiv; [CAS RN 76308-26-4]) was added and stirring continued at 50 0C for 2 h. The solution was concentrated by evaporation under reduced pressure, the pH adjusted to 9 by addition of a solution of 1 M NaHCtheta3 and the aqueous layer extracted with dichloromethane. The combined organic phases were dried over MgStheta4 and concentrated by evaporation under reduced pressure. The crude material was used in the consecutive step without further purification. MS (ISP): 564.7 [M+H]+.

The synthetic route of 76308-26-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BENSON, Gregory Martin; BLEICHER, Konrad; FENG, Song; GRETHER, Uwe; KUHN, Bernd; MARTIN, Rainer E.; PLANCHER, Jean-Marc; RICHTER, Hans; TAYLOR, Sven; WO2010/43513; (2010); A1;,
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Application of 24393-53-1,Some common heterocyclic compound, 24393-53-1, name is (E)-Ethyl 3-(4-bromophenyl)acrylate, molecular formula is C11H11BrO2, 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.

308 mg (0.26 mmol, 5 mol%) of tetrakis(triphenylphosphine)palladium are added to a solution of 2 g (5.34 mmol, 1.0 eq) of 3-heptyl-1-methyl-1-[3-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenyl]urea and 1.6 g (6.4 mmol, 1.2 eq) of ethyl 4-bromocinnamate in 20 mL of an 8/2 mixture of dimethylformamide and of 2M potassium phosphate solution. The reaction mixture is stirred for 3 hours at 90C. The reaction is stopped by addition of 50 mL of water and then extracted with ethyl acetate. The organic phases are combined and dried over sodium sulfate. The solvents are evaporated off and the residue is then chromatographed on silica gel (70/30 heptane/ethyl acetate). 1.69 g of ethyl 3-[3′-(3-heptyl-1-methylureido)biphenyl-4-yl]acrylate in oil form are obtained. Yield = 75 %

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (E)-Ethyl 3-(4-bromophenyl)acrylate, its application will become more common.

Reference:
Patent; GALDERMA RESEARCH & DEVELOPMENT, S.N.C.; WO2006/18326; (2006); A1;,
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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. 19063-56-0, name is 7-Bromo-2H-chromen-2-one belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C9H5BrO2

2-Butyl-6-ethynyl-1H-benz [de]isoquinoline-1,3(2H)-dione 14(0.2 g, 0.722 mmol) and 7-Bromocoumarin (0.16 g, 0.722 mmol) weredissolved in THF-triethylamine (1:1, v/v, 120 mL) and the mixture wasdeaerated for 10 min by bubbling nitrogen gas. Then, Pd(PPh3)2Cl2(10.35 mg, 2 mol%), PPh3 (7.5 mg, 4 mol%) and CuI (2.75 mg, 2mol%)were added. The solution was deaerated for further 5 min; after that,the reaction was left for 8 h under nitrogen atmosphere at 60 C. Aftercompletion of the reaction, the reaction mixture was cooled to roomtemperature and the solvent was evaporated. The crude product wasdissolved in dichloromethane and purified by silica gel column chromatographywith chloroform as eluant. NC 5 was obtained in 60.2%yield (0.18 g), m. p. 252 C. IR (KBr): numax/cm-1 2200 (nuC?C) 1740(nuCO), 1693 (nuCO). 1H NMR (400 MHz, CDCl3) delta8.712 (d, 1H,J=8.40 Hz, aromatic),8.675 (d, 1H, J=7.2 Hz, aromatic),8.59 (d, 1H,J=7.6 Hz, aromatic),8.01 (d, 1H, J=7.60 Hz, aromatic), 7.882 (t, 1H,J=8 Hz, aromatic), 7.74 (d, 1H, J=9.2 Hz, aromatic), 7.62 (s, 1H),7.56-7.55 (m, 2H, aromatic), 6.49 (d, 1H, J=9.6 Hz, aromatic), 4.19(t, 2H, J=7.6 Hz, CH2), 1.77-1.69 (m, 2H, CH2), 1.49-1.41 (m, 2H,CH2), 0.99 (t, 3H, J=7.6 Hz, CH3). 13C (150 MHz, CDCl3) delta163.86,163.61, 160.08, 153.84, 142.59, 132.0, 131.72, 131.55, 131.26,130.23, 128.06, 128.01, 127.81, 127.74, 126.38, 125.70, 123.10,122.82, 119.87, 119.53, 117.60, 96.96, 89.34, 40.38, 30.19, 20.38,13.85. HRMS (m/z): [M+H] calculated for C27H20NO4:422.1392;Found: 422.1399.

The synthetic route of 19063-56-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Reddy, T. Sheshashena; Hwang, Jiyoung; Choi, Myung?Seok; Dyes and Pigments; vol. 158; (2018); p. 412 – 419;,
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Application of 2672-58-4,Some common heterocyclic compound, 2672-58-4, name is Trimethyl benzene-1,3,5-tricarboxylate, molecular formula is C12H12O6, 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.

Take 8.00 g of trimesic acid methyl ester 35 oC dissolved in 80 mL of anhydrous tetrahydrofuran,Under nitrogen protection by a constant pressure funnel was slowly added dropwise to 3.00 g of lithium aluminum hydride and 300 mL of anhydrous tetrahydrofuran mixture,The dropwise addition was carried out in ice-salt bath, and the temperature was restored to room temperature after the addition was completed. The mixture was stirred at reflux for 70 oC for 24 h,The reaction was carried out under magnetically stirred ice bath-reflux integrated nitrogen protection. After the reaction, the reaction was quenched with about 100 mL of distilled water, the mixture was suction filtered, the filter cake was washed three times with 100 mL of methanol, and the filtrate was distilled under reduced pressure ,80 oC vacuum drying, 5.12 g are tribenzyl alcohol(96% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Trimethyl benzene-1,3,5-tricarboxylate, its application will become more common.

Reference:
Patent; Jilin Chemical College; Gao Wenxiu; Wang Jisi; Lou Dawei; Yu Dandan; Zhang Zhihui; Zhang Hao; (9 pag.)CN107501043; (2017); A;,
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These common heterocyclic compound, 57486-69-8, name is Methyl 2-(2-bromophenyl)acetate, 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. Quality Control of Methyl 2-(2-bromophenyl)acetate

2-(2-Bromophenyl)-propionic acid methyl ester:[0275] In a 500 mL round bottom flask, 5.1460g (45.8603 mmol, 2.2 eq) of the potassium t-butoxide was suspended in 190 mL of clean, dry THF under N2 atmosphere. To this was added 4.7751 g (20.8456 mmol, 1.0 eq) of the methyl ester dissolved in 10 mL of THF. The solution immediately became a cloudy yellow. The reaction solution was allowed to stir for thirty minutes at room temperature. To the stirred reaction was then added 2.86 mL (48.8603 mmol, 2.2 eq) of the methyl iodide in one portion. The reaction was allowed to stir overnight at room temperature. The following morning, the reaction was diluted with 200 mL of H20. The layers were separated and the aqueous solution was extracted with EtOAc (2 x 100 mL). The organic layers were combined, washed with brine (1 x 100 mL) and dried overNa2S04. The solvent was removed under reduced pressure, yielding a deep yellow oil. The oil was taken up in EtOAc and concentrated onto Celite. The product was then purified using silica gel column chromatography, eluting a gradient of 100% heptane to 50% EtOAc in heptane. A colorless oil was isolated. LCMS (m/e): 244 (M+H); NMR (400 MHz, acetone- d6) delta ppm 1.44 (d, J=7.17 Hz, 3 H) 3.50 – 3.72 (m, 3 H) 4.20 (q, J=7.18 Hz, 1 H) 7.11 – 7.26 (m, 1 H) 7.37 (d, J=4.73 Hz, 2 H) 7.56 – 7.66 (m, 1 H).

The synthetic route of Methyl 2-(2-bromophenyl)acetate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ANACOR PHARMACEUTICALS, INC.; JACOBS, Robert, T.; CHEN, Daitao; ORR, Matthew; PLATTNER, Jacob, J.; WO2011/116348; (2011); A1;,
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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 6942-39-8 as follows. Recommanded Product: Methyl 2-bromo-5-fluorobenzoate

Example 16a) 2-Bromo-5-dimethylamino-benzoic acid methyl ester (16a)To a stirred solution of 5,24 g (22.5 mmol) 2-Bromo-5-fluoro-benzoic acid methyl ester (Rarechemicals) and 60.0 ml dimethylsulphoxid were added 2.23 g (27.0 mmol) dimethylamine hydrochloride and 6.54 g (47.3 mmol) potassium carbonate. The reaction mixture was stirred for 11 h at 7O0C in an autoclave and was concentrated with high vacuum rotation evaporator at 650C. The residue was diluted with dichloromethane, washed twice with water. The combined water phases were extracted with dichloromethane. The combined dichloromethane phases were washed with diluted sodium hydrogen carbonate solution, dried with sodium sulphate and concentrated. The oily crude was purified by column chromatography and the desired product 16a was obtained in 70 % yield (4,08 g, 15.8 mmol).MS-ESI: 258/560 (M+ +1 , 90/81).Elementary analysis: C 46.53% H 4.69% N 5.43%Determined: C 46,59% H 4.72% N 5.41%

According to the analysis of related databases, 6942-39-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; WO2008/28688; (2008); A2;,
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