Tag: M.W=200-300

Application of 331779-03-4, These common heterocyclic compound, 331779-03-4, name is Ethyl 2-(4-bromophenyl)acrylate, 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 of ester (20 mmol, 1.0 equiv) in toluene (40 mL) was addedparaformaldehyde (1.80 g, 60 mmol, 3.0 equiv), K2CO3 (8.29 g, 60 mmol, 3.0 equiv),n-Bu4NI (370.0 mg, 1.0 mmol, 0.05 equiv). The reaction mixture was heated to 60 Covernight. After the finish of reaction monitored by TLC, the reaction was cooled toroom temperature, water was added and the aqueous layer was extracted with Et2O(40 mL × 3). The combined organic layer was dried over anhydrous Na2SO4,concentrated in vacuo. The resulting residue was purified by column chromatographyto give the corresponding acrylate intermediate as a colorless oil. Then, a solution ofsubstituted amine (20 mmol, 2.0 equiv)in THF (13.0 mL) at 0C was added a solutionof corresponding acrylate (10 mmol, 1.0 equiv) in THF (7.0 mL) via addition funnel.The reaction mixture was allowed to warm to ambient temperature then stirred atroom temperature for 24h, and concentrated under vacuum. The resulting residue waspurified by column chromatography to give the corresponding intermediate as a oil.Then to a solution of the oil in dichloromethane (20.0 mL) were added di-tert-butyldicarbonate (2.40 g, 11 mmol) and DMAP (122.0 mg, 1 mmol), and the mixture wasstirred at room temperature for 24h. Saturated aq. NH4Cl was added to the mixtureand the resulting mixture was extracted with dichloromethane. The combined organiclayer was washed with brine, dried over Na2SO4, filtered and evaporated in vacuo.The resulting residue was purified by column chromatography to give thecorresponding intermediate as a colorless oil. Then to a solution of the resulting oil inTHF/H2O (5 mL/5 mL) was added LiOH (1.20 g, 50 mmol, 5 equiv). The reactionmixture was heated at 60 C overnight. After cooling to room temperature, thereaction was acidified using aqueous HCl (6 M), and the aqueous layer was extractedwith Et2O (20 mL × 3). The combined organic layer was washed with water and brine,dried over Na2SO4, and concentrated in vacuo to give the resulting product 4a-j as acolorless crystal, using for the next step without further purification.

The synthetic route of 331779-03-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Guo, Li; He, Gu; Pan, Zhaoping; Wu, Fengbo; Yu, Meng; Zeng, Minghui; European Journal of Medicinal Chemistry; vol. 189; (2020);,
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Application of 1094227-86-7, These common heterocyclic compound, 1094227-86-7, name is Ethyl 2-(cyclopentylamino)benzoate, 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.

A mixture of ethyl 2-(cyclopentylamino)benzoate (1.40 g, 6.0 mmol), 4 N HCl in dioxane solution (2.25 mL, 9.0 mmol) and 2,4-dichloro-5-nitropyrimidine (1.74 g, 9.0 mmol) in dioxane (40 mL) was heated at 60 C. for 90 hours. After the reaction was complete as monitored by thin layer chromatography (TLC), the reaction solution was concentrated and the residue was purified by silica-gel column chromatography with ethyl acetate and hexane (1/20, v/v) to give the amination product 12 (1.84 g, 79%). MS (ESI) m/z 391 (M+H)+.

Statistics shows that Ethyl 2-(cyclopentylamino)benzoate is playing an increasingly important role. we look forward to future research findings about 1094227-86-7.

Reference:
Patent; DANA-FARBER CANCER INSTITUTE, INC.; Gray, Nathanael S.; Waller, David; Choi, Hwan Guen; Wang, Jinhua; Deng, Xianming; (104 pag.)US2016/24115; (2016); A1;,
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Adding a certain compound to certain chemical reactions, such as: 14062-30-7, name is Ethyl 2-(3-bromophenyl)acetate, 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 14062-30-7, name: Ethyl 2-(3-bromophenyl)acetate

(3-Cyano-phenyl)-acetic acid ethyl ester. A mixture of (3-bromo-phenyl)-acetic acid ethyl ester (9.15 g, 37.6 mmol), copper cyanide (5.06 g, 56.5 mmol), and 1-methyl-2-pyrrolidinone (80 mL) was placed into an oil bath heated at 120 C. behind a protective shield. The reaction was heated to 200 C. for 1 h and additional copper cyanide (spatula tip) was added. After heating for an additional 0.5 h, the reaction was cooled to room temperature. The reaction was diluted with EtOAc and the organic solution was washed with water/ammonium hydroxide solution (2:1 v/v) until the aqueous solution was no longer blue. The organic solution was washed with brine, dried (MgSO4), filtered, and concentrated. Flash chromatography (9:1 hexanes:EtOAc) provided (3-cyano-phenyl)-acetic acid ethyl ester (6.31 g) as a clear oil which solidified on standing. 1H NMR (400 MHz, CDCl3) delta 7.57-7.50 (m, 3H), 7.42 (m, 1H), 4.15 (q, 2H), 3.63 (s, 2H), 1.24 (t, 3H).

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

Reference:
Patent; Pfizer Inc.; US6288120; (2001); B1;,
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Synthetic Route of 57486-69-8,Some common heterocyclic compound, 57486-69-8, name is Methyl 2-(2-bromophenyl)acetate, molecular formula is C9H9BrO2, 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 2-5 mL capacity microwave vial was charged methyl 2-(2-bromophenyl)acetate (0.100g, 0.43 mmol), 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (0.115 g, 0.523 mmol)and cesium carbonate (0.280 g, 0.86 mmol) in anhydrous 1,2-dimethoxy ethane (4 mL). Themixture was stirred and degassed with argon for 5 min. To this mixture was added Pd(PPh3)4(25 mg, 0.021 mmol) under argon atmosphere, and purged for 2 min. The tube was sealedand irradiated in microwave at 125 C for 0.5 h (This is the internal temperature of reactionmixture and monitored on the screen through a sensor). The vial was cooled to 0C over aperiod of 15 min, followed by addition of 1M potassium tert-butoxide (0.65 mL, 0.65 mmol)solution in THF. The resulting mixture was stirred for 10 minutes and quenched withsaturated ammonium chloride solution. The mixture was diluted with ethyl acetate (30 mL)and washed with water and brine. The organic layer was dried over anhydrous sodiumsulfate, filtered and concentrated. The residue obtained was purified by flash columnchromatography by eluting with gradient of 2-20% ethyl acetate in hexane to afford the 5Hdibenzo[b,d]azepin-6(7H)-one (4) as off white solid (0.075 g, 82%).

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-bromophenyl)acetate, its application will become more common.

Reference:
Article; Deb, Prasant K.; Sharma, Somesh; Borude, Avinash; Singh, Ravi P.; Kumar, Deepak; Reddy, L. Krishnakanth; Tetrahedron Letters; vol. 54; 23; (2013); p. 2916 – 2919;,
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Electric Literature 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.

To a solution of (£ ethyl 3-(4-bromophenyl)acrylate (10.0 g, 39.2 mmol) in THF (150 mL) was slowly added at -78 C a solution of DIBA1-H (86 mL of 1M solution in hexanes, 86.0 mmol). The resulting solution was then allowed to slowly warm to 0 C, after which a further 10 mL of DIBA1-H solution was added. TLC analysis indicated complete reaction and the mixture was re-cooled to -78 C. MeOH was then slowly added to quench the remaining reducing agent and the mixture allowed to warm back to rt over 30 minutes. The resulting mixture was poured into a saturated aqueous solution of Rochelle’s salt and then extracted with EtOAc. The organic phase was separated, dried (MgSO i), filtered and the filtrateconcentrated in vacuo. The crude product thus obtained was purified on silica eluting with a gradient of 0 to 35% EtOAc in hexanes to afford 6.0 g (71%) of (£)-3-(4-bromophenyl)prop-2-en-l-ol.

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; INCEPTION 2, INC.; STOCK, Nicholas, Simon; CHEN, Austin, Chih-Yu; BRAVO, Yalda, Mostofi; JACINTHO, Jason, Duarte; SCOTT, Jill, Melissa; STEARNS, Brian, Andrew; CLARK, Ryan, Christopher; TRUONG, Yen, Pham; WO2013/134562; (2013); A1;,
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Electric Literature of 6942-39-8,Some common heterocyclic compound, 6942-39-8, name is Methyl 2-bromo-5-fluorobenzoate, molecular formula is C8H6BrFO2, 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.

a) 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 are added 2.23 g (27.0 mmol) dimethylamine hydrochloride and 6.54 g (47.3 mmol) potassium carbonate. The reaction mixture is stirred for 11h at 70C in an autoclave and is concentrated with high vacuum rotation evaporator at 65C. The residue is diluted with dichloromethane, washed twice with water. The combined water phases are extracted with dichloromethane. The combined dichloromethane phases are washed with diluted sodium hydrogen carbonate solution, dried with sodium sulphate and concentrated. The oily crude is purified by column chromatography and the desired product 16a is obtained in 70 % yield (4,08 g, 15.8 mmol). MS-ESI: 258/560 (M+ +1, 90/81).

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-bromo-5-fluorobenzoate, its application will become more common.

Reference:
Patent; Bayer Schering Pharma Aktiengesellschaft; EP1897885; (2008); 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. 2672-58-4, name is Trimethyl benzene-1,3,5-tricarboxylate, A new synthetic method of this compound is introduced below., Formula: C12H12O6

EXAMPLE 5 STR20 1,3,5-tris(hydroxymethyl)benzene To a stirring solution of trimethyl 1,3,5-benzenetricarboxylate (10.45 g, 41.4 mmol) in 70 ml of anhydrous THF is added at room temperature a 10M solution of borane-methyl sulfide complex (25 ml, 248 mmol) and the solution is heated to reflux for 3 h. The mixture is then added slowly to 50 ml of MeOH and the resulting mixture is heated at 70 C. for 10 min to remove the methyl sulfide. Evaporation of solvent, washing twice with 50 ml of MeOH and evaporation of MeOH gives 1,3,5-tris(hydroxymethyl)benzene (6.96 g, 100%). 1 H NMR (D2 O): delta 4.52 (6H, s), 7.15 (3H, s).

The synthetic route of 2672-58-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck Frosst Canada & Co.; US6121253; (2000); A;,
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Related Products of 636-53-3, These common heterocyclic compound, 636-53-3, name is Diethyl isophthalate, 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.

Will 6.8Kg of diethyl isophthalate, 24.0 kg of 2,2,6,6-tetramethyl-4-aminopiperidine was added to a 50 liter reactorIn the reactor all the materials off the entrance. The reaction was carried out at 190 C for 2 hours and then at 230 C for 6 hours. The temperature was lowered to below 180 C, and excess 2,2,6,6-tetramethyl-4-aminopiperidine was recovered by vacuum distillation under a vacuum pump. Then use water to generateN, N’-bis (2,2,6,6-tetramethyl-4-piperidinyl) -1,3-benzenedicarboxamide, filtered and dried to give 12.4 kg of acicular white crystalline product , Yield 91.6%.

Statistics shows that Diethyl isophthalate is playing an increasingly important role. we look forward to future research findings about 636-53-3.

Reference:
Patent; Xiangtan University; Luo Zhiqiang; Zhang Lingjun; Zhang Jing; Ji Yongsheng; Ji Changfu; Zeng Yang; Liu Mengyan; Zhou Ji; Liu Minna; Wang Zhe; (7 pag.)CN106905225; (2017); A;,
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Synthetic Route of 79432-87-4, A common heterocyclic compound, 79432-87-4, name is (E)-Methyl 3-(3-bromophenyl)acrylate, molecular formula is C10H9BrO2, 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 dry flask were added (E) -methyl 3- (3-bromophenyl) acrylate (1.18 g, 4.89 mmol) , methanol (10 mL) and 10%Pd/C (120 mg) in turn, the mixture was stirred at 40 under H2for 6 hours. The mixture was filtered and the filtrate was concentrated in a rotary evaporator to get the title compound as a brown liquid (1.2 g, 100%) . ESI: (ESI, pos. ion) m/z: 243.1 [M+H]+.

The synthetic route of 79432-87-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; LIU, Xinchang; REN, Qingyun; YAN, Guanghua; GOLDMANN, Siegfried; ZHANG, Yingjun; (253 pag.)WO2019/76310; (2019); 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 61500-87-6 as follows. Safety of Methyl 2-amino-4-(trifluoromethyl)benzoate

General procedure: To a solution of methyl 2-amino-4-fluorobenzoate (1.64 g, 9.71 mmol) and methanesulfonyl chloride (5.28 mL, 115 mmol) in dichloromethane (100 mL) was added pyridine (7.86 mL, 97.1 mmol). The solution was stirred at room temperature for 18 hours. The reaction was quenched with 1N HCl and was stirred for 5 minutes. The mixture was extracted with DCM (3×). The combined organic layers were washed with brine, dried over anhydrous MgSO4, filtered and concentrated. The crude product was purified by silica gel chromatography to afford methyl 4-fluoro-2-(methylsulfonamido)benzoate.

According to the analysis of related databases, 61500-87-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Gilead Sciences, Inc.; Farand, Julie; Kaplan, Joshua A.; Notte, Gregory; Olen, Casey Lockwood; Sangi, Michael; Sperandio, David; (115 pag.)US2019/359565; (2019); A1;,
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