Month: July 2021

Reference of 618-89-3, 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 618-89-3 as follows.

General procedure: Under inert atmosphere (N2), in a 25 mL round bottom flask, Ar3Bi (0.208 mmol; 0.35 eq.), CsF (0.24 g: 1.8 mmol; 3 eq.), PPh3 (0.004 g: 0.018 mmol; 3 mol%), the aryl bromide (0.60 mmol; 1 eq.) was added to DMF (5 mL). The solution was warmed to 90 C prior addition of PEPPSI IPr (0.012 g: 0.018 mmol; 3 mol%). The reaction was monitored by GC/MS to follow the total consumption of the aryl bromide. Cooled to room temperature (RT), the reaction mixture was diluted by addition of diethyl ether (20 mL) and aqueous HCl 6 M (30 mL). After decantation, the aqueous solution was extracted with diethylether (2 * 20 mL). The collected organic phases were then washed with HCl 6 N (2 * 25 mL), water (25 mL) and brine (25 mL) prior drying over MgSO4. After concentration under reduced pressure, the resulting crude product was subjected to purification by column chromatography leading after concentration under reduced pressure to the title compound.

According to the analysis of related databases, 618-89-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Cassirame, Benedicte; Condon, Sylvie; Pichon, Christophe; Journal of Molecular Catalysis A: Chemical; vol. 425; (2016); p. 94 – 102;,
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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. 13831-03-3, name is tert-Butyl propiolate, A new synthetic method of this compound is introduced below., Quality Control of tert-Butyl propiolate

General procedure: Into an oven-dried reaction flask under Ar gas protection was added oxabicyclic alkene (0.2 mmol), Au catalyst (0.001 mmol), methyl propiolate (0.4 mmol) and toluene (1.0 mL). The reaction mixture was stirred at room temperature normally overnight. After complete consumption of the starting materials, monitored by TLC, the solvent was removed under reduced pressure and the residue was purified by flash column chromatography.

The synthetic route of 13831-03-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sun, Yin-Wei; Xu, Qin; Shi, Min; Beilstein Journal of Organic Chemistry; vol. 9; (2013); p. 1969 – 1976;,
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Reference of 346603-63-2, The chemical industry reduces the impact on the environment during synthesis 346603-63-2, name is Methyl 2-methyl-3-(trifluoromethyl)benzoate, I believe this compound will play a more active role in future production and life.

To a 1 L round bottom flask equipped with a stir bar, nitrogen lines, and pressure equalizing addition funnel, was added lithium aluminum deuteride (LAD) (12 g, 286 mmol). The solid material was taken up in anhydrous tetrahydrofuran (THF) (268 ml) and the resulting suspension placed under a nitrogen atmosphere and the temperature lowered to 0 0C. The addition funnel was then charged with a solution of methyl 2-methyl-3- (trifluoromethyl)benzoate (27 g, 124 mmol) in anhydrous tetrahydrofuran (THF) (107 ml), and the substrate was slowly added, drop-wise, to the LAD suspension over approximately 30 minutes. Upon complete addition, the funnel was removed and the inert atmosphere maintained. The reaction temperature was allowed to warm naturally to ambient over 2 hours with vigorous stirring. The reaction was then quenched with a modified Fieser and Fieser workup (adjusting by multiplying normal lithium aluminum hydride reduction workup amount by .8564) by sequential addition of the following: 10.277 mL water, 10.277 mL of 15 wt % NaOH (aq.) solution, and 30.83 mL water. The resulting mixture was stirred at room temperature for 1 hour to allow the precipitate to form and was then filtered, followed by concentration of the solution, in vacuo, to afford a gel. The gel was suspended in dichloromethane and transferred to a 100 mL round bottom flask. The material was concentrated to a gel and then subjected to high vacuum to afford [2-methyl- 3-(trifluoromethyl)phenyl]methanol-d2 (21.883 g, 114 mmol, 92 % yield) as a white solid 1H NMR (400 MHz, DMSO-J6) delta ppm 2.33 (d, J=I.52 Hz, 3H) 5.26 (s, IH) 7.37 (t, J=7.71 Hz, IH) 7.57 (d, J=7.83 Hz, IH) 7.67 (d, J=7.83 Hz, IH).

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, Methyl 2-methyl-3-(trifluoromethyl)benzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXOSMITHKLINE LLC; LIN, Hong; LUENGO, Juan, I.; RIVERO, Ralph, A.; SCHULZ, Mark, James; XIE, Ren; ZENG, Jin; WO2010/135504; (2010); A1;,
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These common heterocyclic compound, 145576-28-9, name is Ethyl 4-methylenecyclohexanecarboxylate, 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. Application In Synthesis of Ethyl 4-methylenecyclohexanecarboxylate

Ethyl 4-methylidenecyclohexanecarboxylate (50 mg, 0.3 mmol) was stirred with 0.5M 9-borabicyclo[3.3.1]nonane in THF (0.89 mL), which was added slowly undernitrogen. The reaction mixture was stirred at room temperature overnight. The crude mixture was cooled to 0C and Intermediate 29 (203 mg, 0.51 mmol) in DMF (3 mL) was added, followed by bis[3 -(diphenylphosphanyl)cyclopenta-2,4-dien- 1 -yl] iron dichloropalladium dichloromethane complex (24 mg, 0.03 mmol) and 2M aqueous potassium carbonate solution (0.22 mL). The reaction mixture was stirred at room temperature overthe weekend, then heated at 60C for 1.5 h. Further bis[3-(diphenylphosphanyl)- cyclopenta-2,4-dien- 1 -yl]iron dichloropalladium dichloromethane complex (50 mg, 0.061 mmol) was added and the mixture was heated at 80C overnight under nitrogen. The reaction mixture was added to cold water and 0.5M aqueous NaOH solution (0.5 mL) was added. The mixture was extracted with DCM (100 mL), dried over sodium sulphate,filtered and concentrated under vacuum. The resulting brown oil was purified twice by FCC, eluting with 0-30% MeOH in DCM. The material was further purified by preparative HPLC (Method C), to afford the title compound (11.4 mg, 7%) as a brown oil. Method B HPLC-MS: MH+ m/z 535, RT 1.72 minutes.

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

Reference:
Patent; UCB PHARMA S.A.; BENTLEY, Jonathan Mark; BROOKINGS, Daniel Christopher; BROWN, Julien Alistair; CAIN, Thomas Paul; CHOVATIA, Praful Tulshi; FOLEY, Anne Marie; GALLIMORE, Ellen Olivia; GLEAVE, Laura Jane; HEIFETZ, Alexander; HORSLEY, Helen Tracey; HUTCHINGS, Martin Clive; JACKSON, Victoria Elizabeth; JOHNSON, James Andrew; JOHNSTONE, Craig; KROEPLIEN, Boris; LECOMTE, Fabien Claude; LEIGH, Deborah; LOWE, Martin Alexander; MADDEN, James; PORTER, John Robert; QUINCEY, Joanna Rachel; REED, Laura Claire; REUBERSON, James Thomas; RICHARDSON, Anthony John; RICHARDSON, Sarah Emily; SELBY, Matthew Duncan; SHAW, Michael Alan; ZHU, Zhaoning; WO2014/9295; (2014); A1;,
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Reference of 1186-73-8,Some common heterocyclic compound, 1186-73-8, name is Trimethyl methanetricarboxylate, molecular formula is C8H12O6, 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.

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 15.8g(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-0.2g tri-ssterdibanzyl biotin (95.3% of the theoretical value), and the HPLC measured content is 98.0% with no impurity 5 (hereinafter to be referred as dicarboxylic ester).

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

Reference:
Patent; Zhejiang Medicine Co., Ltd.; EP2433942; (2012); 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 175867-59-1 as follows. Product Details of 175867-59-1

((R)-4-(5-(4-chlorophenyl)-1-ethyl-4-(3-(4-(4-(4-(4-(4-hydroxypiperidin-1-yl)-1-(phenylthio)butan-2-ylamino)-3-(trifluoromethylsulfonyl)phenylsulfonamido)phenyl)piperazin-1-yl)phenyl)-2-methyl-1H-pyrrole-3-carboxamido)cyclohexanecarboxylic acid (10) To a solution of BM-957 (100 mg, 0.09 mmol), EDCI (27 mg, 0.14 mmol) and HOBT (19 mg, 0.14 mmol) in DCM (2 mL) was added methyl 4-aminocyclohexanecarboxylate (44 mg, 0.28 mmol). The solution was stirred for 2 hours at room temperature until no BM-957 was observed by TLC. The reaction mixture was diluted with ethyl acetate (50 mL), washed with saturated NaHCO3 solution (50 mL), brine (50 mL) and dried over sodium sulfate. The solvent was removed in vacuo to give crude product which was used for next step without purification. The resulting residue was dissolved in H2O and MeOH (5 mL and 5 mL respectively) and followed by adding NaOH (76 mg, 1.9 mmol). The solution was stirred at room temperature for 20 h until no starting material was observed by TLC. The reaction mixture was concentrated in vacuo and the residue was purified by HPLC to give the pure product 10 (salt with TFA, 61 mg, yield 55% over two steps). The gradient ran from 60% of solvent A and 40% of solvent B to 20% of solvent A and 80% of solvent B in 40 min. MS (ESI): m/z 1191.17 (M+H)+.

According to the analysis of related databases, 175867-59-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; Wang, Shaomeng; Chen, Jianfang; McEachern, Donna; Bai, Longchuan; Liu, Liu; Sun, Duxin; Li, Xiaoqin; Aguilar, Angelo; US2014/199234; (2014); 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. 5121-34-6, name is Methyl 2-amino-3-methoxybenzoate, A new synthetic method of this compound is introduced below., category: esters-buliding-blocks

Step A:; To a solution of 2-amino-3-methoxybenzoate (1.62 g, 8.97 mmol) in DMF (15 mL) was added N-bromosuccinimide (1.76 g, 9.87 mmol). The resulting mixture was stirred at room temperature for 2 h. The reaction mixture was diluted with ether and water. The aqueous layer was isolated and extracted with ether (2×100 mL). The combined organic layers were washed with water (2×100 mL), brine, dried over Na2SO4, filtered and concentrated to afford a brown solid. The crude material was purified by column chromatography (silica gel, 95:5 hexanes/ethyl acetate) to afford the desired product (2.08 g, 89%) as a light orange solid: 1H NMR (300 MHz, CDCl3) delta 7.60 (d, J=2.1 Hz, 1H), 6.90 (d, J=2.1 Hz, 1H), 6.03 (br s, 2H), 3.86 (s, 6H); MS (ESI+) m/z 259 (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; AMR Technology, Inc.; US2006/183769; (2006); A1;,
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Related Products of 106896-49-5, 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. 106896-49-5, name is Methyl 4-amino-3-bromobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: An over-dried vial equipped with stir bar was charged with Pd(OAc)2 (0.0055 g, 0.0245mmol, 0.10 equiv.), dppb (0.020 g, 0.0489 mmol, 0.2 equiv.) and K2CO3 (0.15 g, 0.98 mmol, 4.0equiv.). Freshly distilled toluene was introduced into the vial via syringe and the contents were allowed to stir. A second over-dried vial equipped with a stir bar was charged with cyclopropanol (0.05 g, 0.245 mmol, 1.0 equiv.) and 2-bromoaniline (0.084 g, 0.489 mmol, 2.0equiv.). Freshly distilled toluene was introduced into the vial via syringe and contents allowed to stir. The solution of substrates was added to the solution containing the palladium catalyst. The reaction vial was purged with argon, capped with a rubber septum and heated to 110 C for 24hrs. Upon completion, the reaction mixture was filtered through a pad of celite using EtOAc, and concentrated in vacuo. The crude product was purified by flash column chromatography, eluting with the indicated solvent mixture to afford the desired quinoline product. Purification by flash column chromatography using 20% EtOAc in hexanes provided the desired quinoline as a pale yellow oil (0.051 g, 0.19 mmol) in 76% yield

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, Methyl 4-amino-3-bromobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Nikolaev, Andrei; Nithiy, Nisha; Orellana, Arturo; Synlett; vol. 25; 16; (2014); p. 2301 – 2305;,
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Electric Literature of 28868-76-0,Some common heterocyclic compound, 28868-76-0, name is Dimethyl 2-chloromalonate, molecular formula is C5H7ClO4, 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.

c) 18.2 g of 2-chloro-5-methoxyphenol were dissolved in 150ml of dry methanol. 9.3 g of MeONa followed by 25 g of dimethyl chloromalonate were added. The reaction mixture was stirred at 50 C. for 2 hours. After distillation of the solvent the residue was partitioned between toluene and H2 O in a separating funnel and washed neutral. After crystallization in ethanol there was obtained dimethyl (2-chloro-5-methoxy)phenoxy-malonate, white crystals with m.p. 68-69 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Dimethyl 2-chloromalonate, its application will become more common.

Reference:
Patent; Hoffmann-La Roche Inc.; US5541186; (1996); A;,
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Electric Literature of 14062-18-1, 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 14062-18-1 as follows.

General procedure: In a glove box, add a ruthenium complex Ia (0.3 to 0.7 mg, 0.0002 to 0.001 mmol) to a 300 mL autoclave,Potassium methoxide (35-700 mg, 0.5-10 mmol), tetrahydrofuran (4-60 mL), and ester compounds (10-200 mmol).After sealing the autoclave, take it out of the glove box and fill it with 50 100atm of hydrogen.The reaction kettle was heated and stirred in an oil bath at 100 C for 10 to 336 hours.After the reaction kettle was cooled in an ice-water bath for 1.5 hours, the excess hydrogen was slowly released.The solvent was removed from the reaction solution under reduced pressure, and the residue was purified with a short silica gel column to obtain an alcohol compound. The results are shown in Table 5.

According to the analysis of related databases, 14062-18-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Zhejiang Zhongke Chuangyue Pharmaceutical Co., Ltd.; Ding Kuiling; Tang Yitian; Han Zhaobin; (55 pag.)CN110357923; (2019); A;,
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