Tag: M.W=200-300

Application of 33491-30-4, These common heterocyclic compound, 33491-30-4, name is 8-Bromo-2H-chromen-2-one, 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: General synthetic procedure for 3a/3b/3c: 6-Bromocoumarin(0.5 g, 2.23 mmol), (4-ethynyl)benzaldehyde (0.29 g, 2.23 mmol)were dissolved in THF-triethylamine (1:1, v/v, 120 mL) and themixture was deaerated for 10 min with nitrogen bubbling and thenPd(PPh3)2Cl2 (31 mg, 2mol%), PPh3 (23 mg, 4 mol%)and CuI (8 mg,2mol%) were added. The solution was deaerated for an additional5 min; after that, reaction was left under nitrogen at 60C for 12 h.After completion of the reaction, the reaction mixture was cooledat room temperature and the solvent was evaporated. The crudeproduct was dissolved in CH2Cl2 and purified by a columnchromatography on a silica gel using (chloroform) as an eluent.

Statistics shows that 8-Bromo-2H-chromen-2-one is playing an increasingly important role. we look forward to future research findings about 33491-30-4.

Reference:
Article; Reddy, T. Sheshashena; Choi, Myung-Seok; Journal of Photochemistry and Photobiology A: Chemistry; vol. 351; (2018); p. 108 – 114;,
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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. 432022-88-3, name is Methyl 4-bromo-3,5-dimethylbenzoate, A new synthetic method of this compound is introduced below., SDS of cas: 432022-88-3

II?TERMEDIATE 49 Methyl 4- 5- 14-( (4S,5R)-5 – 13 -fluoro-5-(trifluoromethyl)phenyl] -4-methyl-2-oxo- 1,3 – oxazolidin-3-yBmethyl-2-(methylsulfanylnyrimidin-5-yl1-6-methoxynyridin-3-yB -3.5- dimethylbenzoateA mixture of (4S,5R)-3 – { [5-(5-chloro-2-methoxypyridin-3 -yl)-2-(methylsulfanyl)pyrimidin-4- yl]methyl} -5- [3 -fluoro-5-(trifluoromethyl)phenyl] -4-methyl- 1,3 -oxazolidin-2-one(INTERMEDIATE 18, 211 mg, 0.389 mmol), bis(pinacolato)diboron (296 mg, 1.17 mmol), and potassium acetate (114 mg, 1.17 mmol) in N,N-dimethylacetamide (2.0 mL) was degassed three times with nitrogen gas before the addition of(2-dicyclohexylphosphino-2?,4?,6?-triisopropyl- 1,1 ?-biphenyl) [2-(2-aminoethyl)phenyl)]palladium(II) chloride (XPHOS Biphenyl Precatalyst) (15.5 mg, 0.0 19 mmol). The system was degassed three times and was then heated to 130 C for24 hours. LC/MS analysis indicated complete conversion to the product, but almost exclusively as the boronic acid. For this reason the crude reaction mixture was taken directly into the next step. Accordingly, methyl 4-bromo-3 ,5-dimethylbenzoate (142 mg, 0.584 mmol), (1,1 bis(di tert-butylphosphino)ferrocene palladium dichloride (24.5 mg, 0.039 mmol), and aqueous potassium carbonate (0.389 mL, 2.0 M) were added. The mixture was degassed, flushed withnitrogen and heated to 100C for 45 minutes. The reaction was diluted with ethyl acetate, washed with water, brine, dried over sodium sulfate, filtered and concentrated. The crude product was purified by column chromatography to afford methyl 4-{5-[4-({(4S,5R)-5-[3-fluoro- 5-(trifluoromethyl)phenyl] -4-methyl-2-oxo- 1,3 -oxazolidin-3-yl} methyl)-2- (methylsulfanyl)pyrimidin-5-yl] -6-methoxypyridin-3 -yl} -3 ,5-dimethylbenzoate (158 mg, 0.236mmol). LCMS (M+H)*: 671.1

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; MERCK SHARP & DOHME CORP.; ACTON, John, J., III; YE, Feng; VACHAL, Petr; SHA, Deyou; DROPINSKI, James, F.; CHU, Lin; ONDEYKA, Debra; KIM, Alexander, J.; COLANDREA, Vincent, J.; ZANG, Yi; ZHANG, Fengqi; DONG, Guizhen; WO2013/165854; (2013); A1;,
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Application of 2672-58-4, 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 2672-58-4 as follows.

Will be bothTrimethyl trimellitateSoluble in methanol, trimethyl t-trimellitate and methanol to the mass ratio of 1:25,The molar ratio of trimethyl terephthalate to KOH was 1: 2,0 stirring 2h,Natural warming to 25 ,(4 × 10ml), dried over MgSO4, and the chloroform was removed by filtration to give 3,5-dichlorophenol, which was washed with water and concentrated in water. Dibutyric acid-1-benzoate..

According to the analysis of related databases, 2672-58-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CNOOC Tianjin Chemical Research and Design Institute Co., Ltd.; CNOOC Energy Development Co., Ltd.; Li, Zhiyuan; Wang, Sufang; Xu, Hui; Ding, Qiuwei; Ding, Shu; Lin, Bei; Yu, Xiaowei; Teng, Houkai; (8 pag.)CN106543083; (2017); 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. 57486-69-8, name is Methyl 2-(2-bromophenyl)acetate, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C9H9BrO2

To a solution of methyl 2-(2-bromophenyl)acetate, 5.00 g (21.8 mmol), in 100 ml. of tetrahydrofuran were added 18-crown-6, 1.44 g (5.5 mmol), iodomethane, 7.35 g (65.5 mmol), and potassium ie f-butoxide, 15.49 g (109.1 mmol). The resulting mixture was stirred at this temperature for 26 hours. The solvent was removed in vacuo and the residue was diluted with ethyl acetate. The resulting solution was washed with water, brine, dried over anhydrous sodium sulfate. The solvent was removed in vacuo and the residue was purified by silica gel column chromatography (petroleum ether:ethyl acetate = 6:1) to give 2.73 g (49%) of the product as a yellow oil. MS (ESIpos): m/z = 257 [M+H]+. LC-MS [Method 4, Water (0.1 %HCOOH)-Acetonitrile, 10%B]: Rt = 1.14 min.

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 57486-69-8.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; WORTMANN, Lars; SAUTIER, Brice; EIS, Knut; BRIEM, Hans; BOeHNKE, Niels; VON NUSSBAUM, Franz; HILLIG, Roman; BADER, Benjamin; SCHROeDER, Jens; PETERSEN, Kirstin; LIENAU, Philip; WENGNER, Antje, Margret; MOOSMAYER, Dieter; WANG, Qiuwen; SCHICK, Hans; (510 pag.)WO2018/172250; (2018); 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. 146307-51-9, name is trans-Methyl 4-((tert-butoxycarbonyl)amino)cyclohexanecarboxylate, This compound has unique chemical properties. The synthetic route is as follows., name: trans-Methyl 4-((tert-butoxycarbonyl)amino)cyclohexanecarboxylate

Step 2: Trans-tert-butyl 4-(hydroxymethyl)cyclohexylcarbamateMethyl trans-4-(tert-butoxycarbonylamino)cyclohexanecarboxylate (55.5 g, 216 mmol) was suspended in ethanol (900 ml) and THF (100 ml) and the mixture was cooled to 5C. Granular calcium chloride (47.9g, 431 mmol) was added portionwise to give a milky suspension. Sodium borohydride (32.6 g, 863 mmol) was added portionwise over 25 mins at 5C. The reaction mixture (white emulsion) was stirred at 5C for 1 hour, the water bath was removed and then the reaction mixture was allowed to warm to room temperature and stirred at room temperature overnight. The reaction mixture was cooled to 10C and 5% potassium carbonate (200 ml) was added dropwise until the pH of the solution was pH11. A colourless precipitate formed which was filtered off. The solid was stirred with ethyl acetate (2000 ml) and water (500 ml). The organic layer was separated and washed with 0.5M HCI (200 ml), then washed with water (2 x 200 ml) and saturated brine (100 ml). The organic solution was dried over anhydrous MgS04, filtered and evaporated to give a white solid The solid was dried under high vacuum overnight to constant weight; [M+H]+230.

According to the analysis of related databases, 146307-51-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ATKINSON Benjamin; BEATTIE David; CULSHAW Andrew James; DEVEREUX Nicholas James; MCKENNA Jeffrey; DALE James; WO2011/92293; A1; (2011);,
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Some common heterocyclic compound, 915213-54-6, name is Ethyl 2-(4,4-difluorocyclohexyl)acetate, molecular formula is C10H16F2O2, 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. category: esters-buliding-blocks

To a solution of ethyl 2-(4-oxocyclohexyl)acetate (0.4 g) in DCM (5 mL) was added Deoxo-Fluor (0.881 mL) and EtOH (0.038 mL). The reaction mixture was stirred at rt for 16 h and then diluted with sat. aHC03 and EtOAc. The organic phase was washed with water, sat. NaCl and dried over anhydrous Na2S04, filtered and dried to yield ethyl 2-(4,4-difluorocyclohexyl)acetate (0.4 g). To a solution of ethyl 2-(4,4-difluorocyclohexyl) acetate in THF/MeOH (2 mL) was added IN NaOH (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 IN HCl. The organic phase was washed with sat. NaCl, dried over anhydrous Na2S04, filtered and concentrated to yield 2-(4,4-difluorocyclohexyl)acetic acid as a yellow solid. 1H NMR (400 MHz, DMSO-i) ppm 12.13 (1 H, br. s.), 2.06 – 2.28 (3 H, m), 1.92 – 2.03 (1 H, m), 1.72 – 1.91 (4 H, m), 1.31 – 1.48 (1 H, m), 1.10 – 1.31 (2 H, m).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 915213-54-6, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; HEWAWASAM, Piyasena; LOPEZ, Omar D.; TU, Yong; WANG, Alan Xiangdong; XU, Ningning; KADOW, John F.; MEANWELL, Nicholas A.; GUPTA, Samayamunthula Venkata Satya Arun Kumar; KUMAR, Indasi J. Gopi; PUNUGUPATI, Suresh Kumar; BELEMA, Makonen; WO2015/5901; (2015); 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 139911-28-7 as follows. Computed Properties of C9H8BrFO2

Example 2 – ethyl 2-cyano-5-fluorobenzoateZinc cyanide (26.5 g; 0.225 mol) and Pd2(dba)3 (1.9 g; 3.4 mmol) were added to a solution of ethyl 2-bromo-5-fluorobenzoate (27.9 g; 0.112 mol) in DMF (71 ml). Triphenyl phosphine (2.9 g; 1 1 mmol) was added and then the reaction mixture was stirred at 130C under nitrogen atmosphere for 4 hours. The mixture was poured out into H2O (300 ml) and then extracted with EtOAc (200 ml). The organic layer was separated, washed with H2O (2 x 100 ml), brine (100 ml), dried (MgS04), filtered and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: hexanes/ EtOAc (5/1, v/v)). The product fractions were collected and the solvent was evaporated.Yield: 20 g (93%; orange solid).

According to the analysis of related databases, 139911-28-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ELANCO ANIMAL HEALTH IRELAND LIMITED; THURING, Johannes, Wilhelmus J.; WO2012/112345; (2012); A1;,
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Reference of 10328-87-7, 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. 10328-87-7, name is Methyl 2,3-Dichlorophenylacetate, This compound has unique chemical properties. The synthetic route is as follows.

Step A: Preparation of Methyl 2-(2,3-dichlorophenyl)-2- methylpropanoate; [0472] A solution ofNaH (2.87 g, 71.8 mmol) in DMF (100 mL) was cooled to 00C. A solution of methyl 2-(2,3-dichlorophenyl)acetate (5.24 g, 23.9 mmol) in DMF(50 mL) was added dropwise, and the resulting mixture was stirred for 5 minutes. A solution of MeI (4.36 mL, 69.8 mmol) in DMF (50 mL) was then added to the reaction. After 10 minutes, the mixture was allowed to warm to 25C and the reaction was stirred for 16 hours. The mixture was diluted with 10% HCl(aq) (150 mL), and the resulting mixture was extracted with EtOAc (2×200 mL) and washed with 10% HCl(aq) (100 mL), deionized water (2×150 mL), and brine (100 mL). The organic layer was dried over MgSO4 and concentrated and dried in vacuo to give 7.06g crude product. The crude product was purified by flash column chromatography (silica, 0-50% DCM in hexane) to give the title compound (5.53 g). MS m/e = 247 (M+H)+.

The chemical industry reduces the impact on the environment during synthesis Methyl 2,3-Dichlorophenylacetate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; AMGEN INC.; WO2008/76427; (2008); A2;,
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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. 55954-25-1, name is Methyl 2-(2,4-Dimethoxyphenyl)acetate, A new synthetic method of this compound is introduced below., Application In Synthesis of Methyl 2-(2,4-Dimethoxyphenyl)acetate

General procedure: To a stirred solution of acid 9 (320 mg, 1.76 mmol) in CH2Cl2 (10 mL) under N2 atmosphere, DMF (one drop) and oxalyl chloride (0.23 mL, 2.6 mmol) were added. The mixture was stirred for 3 h at room temperature and then the solvent was removed under vacuum. The crude product acid chloride was directly used for the next reaction without further purification. A solution of compound 1114 (554 mg, 2.64 mmol) in THF (6 mL) was added at -78 C to a freshly prepared solution of LDA, prepared from n-BuLi (2.5 M in THF, 1.44 mL, 3.52 mmol) and i-Pr2NH (0.49 mL, 3.52 mmol) in THF (5 mL) at 0 C under N2 atmosphere. The thus produced yellowish anion was stirred at -78 C for 45 min and then a solution of crude acid chloride in THF (10 mL) was added drop wise. The reaction was stirred at the same temperature for another 45 min and then at room temperature for 4 h. 10% HCl (10 mL) was added to quench the reaction, THF was removed in vacuum and the water layer was extracted with ethyl acetate (2*50 mL). The organic layer was washed with water (2*20 mL), brine (20 mL), dried (Na2SO4) and concentrated. The crude product was purified by silica gel column chromatography to get 12 (500 mg, 76%) as yellowish oily compound.

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; Pahari, Pallab; Saikia, Ujwal Pratim; Das, Trinath Prasad; Damodaran, Chendil; Rohr, Juergen; Tetrahedron; vol. 72; 23; (2016); p. 3324 – 3334;,
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Application of 40640-98-0, The chemical industry reduces the impact on the environment during synthesis 40640-98-0, name is Ethyl 3-(4-bromophenyl)propanoate, I believe this compound will play a more active role in future production and life.

A mixture of a 60% suspension of sodium hydride in mineral oil (4.8 g, 120 mmol) in N, N-dimethylformamide (50 mL) at about 5 C was treated with diethyl malonate (36.4 mL, 240 mmol). The mixture was stirred for about 5 minutes, slowly treated with a solution of 4- bromobenzyl bromide (20.0 g, 80 mmol) in N, N-dimethylformamide (20 mL), stirred at room temperature overnight, diluted with water, and extracted with ethyl acetate. The combined organic extracts were dried (MgS04), filtered, and concentrated under high vacuum. The residue was dissolved in a mixture of acetic acid (46 mL), water (30 mL), and concentrated sulfuric acid (13 mL) and was heated to reflux for 18 hours. The reaction mixture was cooled, concentrated under high vacuum, and diluted with water. The formed crystalline solid was collected by filtration, washed with water and diethyl ether, and was dried under high vacuum to provide the desired product. MS (DCI-NH3) : m/z 246,248 (M+NH4) +.

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 3-(4-bromophenyl)propanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ABBOTT LABORATORIES; MAKOTO, Aoyama; WO2005/95387; (2005); A1;,
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