Month: January 2021

Application of 37746-78-4, The chemical industry reduces the impact on the environment during synthesis 37746-78-4, name is (E)-Ethyl 4-bromobut-2-enoate, I believe this compound will play a more active role in future production and life.

Into a 10-L 4-necked round-bottom flask was placed 2-bromo-4-fluorophenol (500 g, 2.62 mol, 1.00 equiv), N,N-dimethylformamide (5 L), potassium carbonate (1253 g, 9.07 mol, 3.46 equiv), and ethyl (2E)-4-bromobut-2-enoate (1010 g, 5.23 mol, 2.00 equiv). The resulting solution was stirred for 12 h at room temperature. The solids were collected by filtration. The reaction was then quenched by the addition of 15 L of water and extracted with 3×10 L of ethyl acetate. The organic layers were combined and washed with 4×20 L of brine. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1/20). The collected fractions were combined and concentrated under vacuum to give 500 g (63%) of ethyl (2E)-4-(2-bromo-4-fluorophenoxy)but-2-enoate (5) as a white solid.

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, (E)-Ethyl 4-bromobut-2-enoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ACTUATE THERAPEUTICS INC.; ZHANG, Yamin; (72 pag.)WO2019/32958; (2019); A1;,
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Synthetic Route of 27798-60-3, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 27798-60-3 name is Methyl 2-Methoxyphenylacetate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

General procedure: Sodium (10 mmol) was dissolved in 10 mL of absolute methanol, then 4-methylpiperazin-1-yl biguanidine x 2HCl (5 mmol) and the appropriate carboxylic acidester 2e-19e (5 mmol) were added. The reaction mixture was refluxed for 15-30h. After cooling to room temperature, water (10 mL) was added and themixture was stirred for 0.5 h. The precipitated triazine product (2-19) was separated and crystallized from methanol.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 2-Methoxyphenylacetate, and friends who are interested can also refer to it.

Reference:
Article; ?a?ewska, Dorota; Kurczab, Rafa?; Wi?cek, Ma?gorzata; Kami?ska, Katarzyna; Sata?a, Grzegorz; Jastrz?bska-Wi?sek, Magdalena; Partyka, Anna; Bojarski, Andrzej J.; Weso?owska, Anna; Kie?-Kononowicz, Katarzyna; Handzlik, Jadwiga; European Journal of Medicinal Chemistry; vol. 135; (2017); p. 117 – 124;,
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Synthetic Route of 101-97-3, 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. 101-97-3, name is Ethyl 2-phenylacetate, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of ethyl phenylacetate (32.8 g, 200 mmol) in THF (tetrahydrofurane) (1000 mL) under argon was added sodium bistrimethylsilylamide (2M in THF, 100 mL). After 45 minutes, methyl iodide (13 mL) was added over 15 minutes and the mixture was stirred at rt (room temperature) for 30 minutes. Additional sodium bistrimethylsilylamide (2M in THF, 100 mL) was added, followed, after 30 minutes, by methyl iodide (14 mL). After 30 minutes the mixture was diluted with hexane and washed with water. The organic phase was dried, filtered and evaporated to give (1′-ethoxycarbonyl-1′-methyl)ethylbenzene (28.0 g, 146 mmol, 73%).

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

Reference:
Patent; Boehringer Ingelheim Pharmaceuticals, Inc.; EP1171113; (2004); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 98545-64-3, name is Methyl 4-amino-2-bromobenzoate, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C8H8BrNO2

To a solution of compound 21 (3g, 13.0mmol) in AcOH (50mL) was added 2,5-dimethoxytetrahydrofuran (2.15g, 16.3mmol). The mixture was heated to reflux and stirred for 4h. After evaporation, the mixture was dissolved in EtOAc, washed with saturated NaHCO3, and dried over anhydrous Na2SO4. The residue after rotary evaporation was purified by column chromatography over silica gel to give compound 22 as a solid (3.06g, 84.3% yield).1H NMR (400MHz, CDCl3): delta 7.92 (d, J=8.5Hz, 1H), 7.70 (d, J=2.3Hz, 1H), 7.35 (dd, J=8.5, 2.3Hz, 1H), 7.10 (t, J=2.2Hz, 2H), 6.38 (t, J=2.2Hz, 2H) and 3.93 (s, 3H) ppm; mp: 50-53C.

According to the analysis of related databases, 98545-64-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wu, Puhua; Zhang, Jiong; Meng, Qingqing; Nare, Bakela; Jacobs, Robert T.; Zhou, Huchen; European Journal of Medicinal Chemistry; vol. 81; (2014); p. 59 – 75;,
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Adding a certain compound to certain chemical reactions, such as: 135484-83-2, name is Methyl 2-amino-4-bromobenzoate, 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 135484-83-2, Recommanded Product: Methyl 2-amino-4-bromobenzoate

Step 3. Preparation of Methyl 4-bromo-2-isopropoxycarbonylaminobenzoate Add isopropyl chloroformate (104 mL, 104 mmol, 1.0 M in toluene) dropwise to a solution of methyl 2-amino-4-bromobenzoate (14.5 g, 63.0 mmol) and pyridine (10.3 mL, 126.0 mmol) in dichloromethane (210 mL) at room temperature under nitrogen and stir for 5.5 h. Pour the reaction into water (500 mL) and separate the layers. Extract the aqueous layer with dichloromethane (2 x 100 mL) and combine the organic extracts and wash with 2 N HCI, saturated sodium bicarbonate and brine (100 mL each), then dry over sodium sulfate, filter and remove the solvent under reduced pressure to afford the title compound as a pale orange solid (19.2 g, 96%)

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

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/37796; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 126430-46-4, name is Benzyl 4-bromobutanoate, This compound has unique chemical properties. The synthetic route is as follows., Safety of Benzyl 4-bromobutanoate

Compound 11 was synthesized in accordance with the following scheme. Synthesis of compound 10 is disclosed in J. Le Notre et al.. Adv. Synth. Catal. 349, 432 (2007), and synthesis was carried out on the basis thereof. Compound 9 (102.8 mg, 0.347 mmol, 1 eq.) and compound 10 (756.9 mg, 2.94 mmol, 8.5 eq.) were dissolved in acetonitrile (4 mE), N,N-diisopropylethylamine (512 pL, 2.94 mmol, 8.5 eq.) and a small amount of potassium iodide were added, and the mixture was heated and refluxed for 5.5 hours at 80 C. Water was added and then extracted using dichloromethane, the organic phase was washed using water and a saturated sodium chloride solution and dried using anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The resulting residue was purified by medium-pressure silica gel chromatography (eluent:n-hexane/ethyl acetate=86/14 to 65/35) to obtain the objective compound 11(91.7 mg, 56%). 1H NMR (400 MHz, CDCl3): delta 0.45 (s, 6H), 1.93(quin, 2H, J=7.2 Hz), 2.41 (t, 2H, J=7.2 Hz), 2.90 (s, 3H),2.94 (s, 6H), 3.34 (t, 2H, J=7.2 Hz), 3.95 (s, 2H), 5.10 (s,2H), 6.68 (dd, 1H, J=8.4, 2.8 Hz), 6.74 (dd, 1H, J=8.4, 2.8Hz), 6.95 (d, 1H, J=2.8 Hz), 6.99 (d, 1H, J=2.8 Hz), 7.15 (d,1H, J=8.4 Hz), 7.18 (d, 1H, J=8.4 Hz), 7.31-7.36 (m, 5H); 13C NMR (100 MHz, CDCl3): delta-2.7, 22.4, 31.8, 38.6, 39.2,41.2, 52.4, 66.4, 113.8, 114.2, 117.2, 117.3, 117.7, 128.3,128.4, 128.5, 128.65, 128.67, 134.8, 136.0, 136.1, 136.2,147.3, 148.8, 173.2; HRMS (ESI+): Calcd for [M+H]+,473.26188, Found, 473.26185 (-0.0 mmu).

According to the analysis of related databases, 126430-46-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; The University of Tokyo; URANO, Yasuteru; KAMIYA, Mako; MOROZUMI, Akihiko; UNO, Shinnosuke; UMEZAWA, Keitaro; (37 pag.)US2018/52109; (2018); A1;,
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Reference of 1245643-11-1, A common heterocyclic compound, 1245643-11-1, name is Methyl 3,4-diamino-5-bromobenzoate, molecular formula is C8H9BrN2O2, 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.

TsOH?H20 (0.388 g, 2.04 mmol) was added to a mixture of triethylorthoformate (6.8 mL, 40.8 mmol) and methyl 3,4-diamino-5-bromobenzoate (5.0 g, 20.4 mmol) in THF (150 mL). The mixture was stirred at 20C for 5 hours. After cooling to room temperature, the mixturewas concentrated under reduced pressure. EtOAc (20 mL) was added to the crude residue and the mixture was filtered. The filter cake was collected to give methyl 7-bromo- 1H- benzo[d]imidazole-5-carboxylate (4.0 g, 77% Yield) as a pink solid. ?H NMR (400 MHz, DMSO) (5 13.10 (br s, 1H), 8.51 (s, 1H), 8.17 (s, 1H), 7.96 (s, 1H), 3.87 (s, 2H).

The synthetic route of 1245643-11-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; STIVALA, Craig; HEFFRON, Timothy; (243 pag.)WO2019/57946; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 126541-82-0, name is Methyl 3-amino-4-(trifluoromethyl)benzoate, A new synthetic method of this compound is introduced below., Application In Synthesis of Methyl 3-amino-4-(trifluoromethyl)benzoate

Step C: Methyl 3-cyano-4-(trifluoromethyl)benzoateTo a mixture of methyl 3-amino-4-(trifluoromethyl)benzoate (3.2 g, 15 mmol) and aqueous HC1 solution (12 M, 3.5 mL) in water (20 mL) was added dropwise a solution of NaN02 (1.2 g, 17 mmol) in water (7.0 mL) at 5 C. The resulting mixture was stirred for 30 min at 5 C and then added dropwise to a slurry of CuCN (1.3 g, 15 mmol) and KCN (1.6 g, 25 mmol) in water (4 mL), while maintaining the internal temperature between 5-10 C. The mixture was stirred at 10 C for 30 min and then heated at 80 C for 1 h. After cooling, the mixture was extracted with DCM (30 mL x 3). The combined organic layers were washed with brine, dried over Na2S04 and concentrated to afford the title compound. MS: m/z = 230 (M +1). 1H MR (400 MHz, CDC13) delta 8.45-8.53 (m, 1H), 8.33-8.40 (m, 1H), 7.91 (d, 1H, = 8.5 Hz), 4.01 (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.; MITCHELL, Helen; FRALEY, Mark E.; COOKE, Andrew J.; STUMP, Craig A.; BESHORE, Douglas C.; MCCOMAS, Casey C.; SCHIRRIPA, Kathy; ZHANG, Xu-Fang; MCWHERTER, Melody; MERCER, Swati P.; MOORE, Keith; LIU, Chungsing; MAO, Qinghau; (79 pag.)WO2015/143652; (2015); A1;,
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Ester – an overview | ScienceDirect Topics

Reference of 54535-22-7, 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. 54535-22-7, name is Diethyl 2-((phenylamino)methylene)malonate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Compound 23 (4.77 g, 47.7 mmol) was added dropwise to Compound 22 (10 g, 46.3 mmol) with subsurface N2 flow to drive out ethanol below 30 C for 0.5 hours. The solution was then heated to 100-110 C and stirred for 2.5 hours. After cooling the mixture to below 60 C, diphenyl ether was added. The resulting solution was added dropwise to diphenyl ether that had been heated to 228-232 C for 1.5 hours with subsurface N2 flow to drive out ethanol. The mixture was stirred at 228-232 C for another 2 hours, cooled to below 100 C and then heptane was added to precipitate the product. The resulting slurry was stirred at 30 C for 0.5 hours. The solids were then filtered, and the cake was washed with heptane and dried in vacuo to give Compound 25 as a brown solid. 1H NMR (DMSO-d6; 400 MHz) delta 12.25 (s), delta 8.49 (d), delta 8.10 (m), delta 7.64 (m), delta 7.55 (m), delta 7.34 (m), delta 4.16 (q), delta 1.23 (t).

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, Diethyl 2-((phenylamino)methylene)malonate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; VAN GOOR, Fredrick, F.; WO2013/67410; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 85953-29-3, name is Methyl 2-chloro-4-fluorobenzoate, A new synthetic method of this compound is introduced below., Recommanded Product: Methyl 2-chloro-4-fluorobenzoate

A mixture of tert-butyl 4,4′-bipiperidine-l -carboxylate (1-2) (268 mg, 1 mmol, 1.0 eq), methyl 2- chloro-4-fluorobenzoate (5-1) (226 mg, 1.2 mmol, 1.2 eq) and K2CO3 (414 mg, 3 mmol, 3 eq) in NMP (5 ml) was stirred at 120 C for 3 h. After cooling to room temperature, the mixture was diluted with EtOAc (80 niL), washed with water (20 mL x3), brine (10 mL), dried over sodium sulfate and purified by column chromatography (PE:EA =5: 1-3: 1 ) to give tert-butyl l’-(3- chloro-4-(methoxycarbonyl)phenyl)-4,4′-bipiperidine-l-carboxylate (5-2). LRMS m/z (M+Na) 459.2 found, 459.2 required

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.; STACHEL, Shawn, J.; BENNETT, David Jonathan; BRNARDIC, Edward, J.; LIVERTON, Nigel, J.; MANLEY, Peter, J.; MENG, Zhaoyang; NANDA, Kausik, K.; RUDD, Michael, T.; WAI, Jenny; (137 pag.)WO2017/83219; (2017); A1;,
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