Tag: M.W=200-300

Application of 706791-83-5, 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. 706791-83-5 name is Methyl 3-amino-5-bromobenzoate, 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.

To a solution of methyl 3-amino-5-bromobenzoate (61b, 219 mg, 0.950 mmol) in 1,4-dioxane (20 mL) were added bis(pinacolato)diboron (290 mg, 1.14 mmol), PdCl2(dppf) (23 mg, 28.5 pmol) and potassium acetate (279 mg, 2.85 mmol), and then this reaction mixture was stirred at 95 C for 15 h. The reaction mixture was partitioned ethyl acetate (20 mL) and water (10 mL), and the aqueous layer was extracted with ethyl acetate (10 mL x 2). The combined organic layer was washed brine (5 mL), dried over MgS04, filtered and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=4: l) to afford compound 62 (180 mg, 68%) as a white solid; NMR (400 MHz, CDC13) d 7.88 (s, 1H), 7.46 (s, 1H), 7.31 (d, J =2.4 Hz, 1H), 3.91 (s, 3H), 1.36 (s, 12H); MS (ESI, m/z) 278.2 [M+l]+; ESI-HRMS calcd. m/z for (0572) Ci4H2iN04nB 278.1564, found 278.1565 [M+l]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 3-amino-5-bromobenzoate, and friends who are interested can also refer to it.

Reference:
Patent; THE UNITED STATES OF AMERICA, AS REPRESENTED BY THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES; JACOBSON, Kenneth A.; YU, Jinha; CIANCETTA, Antonella; WEN, Zhiwei; JUNG, Young-Hwan; (124 pag.)WO2019/157417; (2019); 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. 52787-14-1, name is Methyl 4-(2-methoxy-2-oxoethyl)benzoate, A new synthetic method of this compound is introduced below., Computed Properties of C11H12O4

Under argon protection, 323g of PLQS-1 and 2.26L of THF were added to a 5L three-necked flask. When the temperature was lowered to -10C, 224ml of 3-bromopropyne was poured into the reaction flask, and the temperature was stirred for 0.5h to start dropping. 1.8L 1mol/L. LiHMDS solution in THF, control the dropping rate, and keep the reaction temperature at -10±3C (about 2~3h). After completion of the addition, stirring was continued for 0.5 h. HPLC detection was completed. After the reaction was completed, the reaction solution was poured into 1.25 L of acetic acid aqueous solution, stirred for 10 minutes, and then liquid-separated. The organic phase was concentrated under reduced pressure at 50 C. to remove the solvent, and the solution was concentrated. About 1.3L of isopropanol was added, and the precipitated solid was stirred and put into 0 to 5C.Cold bathThe mixture was stirred for 3 to 4 hours, filtered, and the filter cake was washed with about 300 ml of a mixed solvent of isopropanol:n-heptane = 1:6. The filter cake was dried in an oven at 50 C. to give 332 g of a pale yellow solid with a yield of 87.0%. The intermediate alpha-propargyl-(4-Methyl formate)-methyl phenylacetate (PLQS-2)The HPLC assay content is 99.6%.The HPLC content of the dipropargyl substituent was 0.3%.

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; Shandong New Age Pharmaceutical Co., Ltd.; Zhang Guimin; Chen Chengfu; Wei Chuanbing; (7 pag.)CN107488112; (2017); A;,
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Related Products of 136333-97-6,Some common heterocyclic compound, 136333-97-6, name is Methyl 4-(2-bromoethyl)benzoate, molecular formula is C10H11BrO2, 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.

Example 11A Diallyl 2-[4-(methoxycarbonyl)benzyl]-2-{2-[4-(methoxycarbonyl)phenyl}ethyl]malonate At room temperature, 62.66 g (192 mmol) of cesium carbonate and 46.75 g (154 mmol) of methyl 4-(2-bromoethyl)benzoate [CAS Reg. No. 136333-97-6] are added to a solution of 42.61 g (128 mmol) of diallyl 2-(4-methoxycarbonylbenzyl)malonate in 450 ml of DMF. The mixture is then stirred at room temperature overnight. After the reaction has gone to completion, the reaction solution is evaporated to dryness, and the residue is taken up in water and extracted three times with ethyl acetate. The combined organic phases are then washed with saturated sodium chloride solution and dried over sodium sulfate. After filtration, the solvent is removed to dryness under reduced pressure. The crude product obtained is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 13:1). This gives 41.35 g (83.6 mmol, 65% of theory) of a colorless solid. LC-MS (Method 2): Rt=2.92 min; m/z=495 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 4-(2-bromoethyl)benzoate, its application will become more common.

Reference:
Patent; Hahn, Michael; Becker, Eva-Maria; Knorr, Andreas; Schneider, Dirk; Stasch, Johannes-Peter; Schlemmer, Karl-Heinz; Wunder, Frank; Lang, Dieter; US2010/197680; (2010); A1;,
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Application of 174579-31-8, These common heterocyclic compound, 174579-31-8, name is tert-Butyl 2-(4-aminophenyl)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.

Synthesis of compound 2.6. A solution of compound 2.5 (1.0 g, 3.19 mmol, 1.0 eq), tert-butyl 2-(4-aminophenyl)acetate (0.661g, 3.19 mmol, 1.00 eq) and K2C03 (1.32 g, 9.57 mmol, 3.0 eq) in DMF (10.0 mL) was heated at 90 C for 12 hours. Upon completion, the mixture was cooled to room temperature and poured into water. The product was extracted with ethyl acetate (50mL X 3). And the combined organic layers were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The crude material was purified using flash column chromatography to afford the compound 2.6 (1.10g, 71.4%) MS (ES): m/z 484.2 [M+H]+.

The synthetic route of 174579-31-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NIMBUS LAKSHMI, INC.; MASSE, Craig E.; GREENWOOD, Jeremy Robert; ROMERO, Donna L.; HARRIMAN, Geraldine C.; WESTER, Ronald T.; SHELLEY, Mee; KENNEDY-SMITH, Joshua Jahmil; DAHLGREN, Markus; WO2015/131080; (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 541-16-2 as follows. Recommanded Product: 541-16-2

Compound 185a (3.15 g, 8.39 mmol) was dissolved in 50 mL of tetrahydrofuran,3.81 mL of tert-butoxycarboxylic anhydride (i.e., di-tert-butyl dicarbonate Boc2O, 16.78 mmol) and 100 mg of p-dimethylaminopyridine,Room temperature reaction 4h.The residue was purified by column chromatography, eluting with petroleum ether: ethyl acetate = 20: 1 (v / v) to give 3.18 g of compound 185b in 91% yield.

According to the analysis of related databases, 541-16-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Ocean University of China; Key Laboratory of Chemistry for Natural Products of Guizhou Province Chinese Academy of Sciences; Zhu, Weiming; Ma, Hongguang; Wang, Liping; Xu, Zhihong; Zhang, Yapeng; Wang, Yi; Liu, Peipei; (142 pag.)CN106083830; (2016); A;,
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Related Products of 685892-23-3, 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. 685892-23-3, name is Methyl 2-bromo-6-chlorobenzoate, This compound has unique chemical properties. The synthetic route is as follows.

Intermediate 4; 4′-{(R)-1-[(3-Amino-oxetane-3-carbonyl)-amino]-ethyl}-3-chloro-3′-fluoro-biphenyl-2-carboxylic acid methyl ester Step A: 4′-((R)-1-tert-Butoxycarbonylamino-ethyl)-3-chloro-3′-fluoro-biphenyl-2-carboxylic acid methyl ester A mixture of {(R)-1-[2-fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-ethyl}-carbamic acid tert-butyl ester (600 mg, 1.64 mmol, intermediate 13), methyl 2-bromo-6-chlorobenzoate (430 mg, 1.72 mmol) [CAS 685892-23-3; commercially available], tri-o-tolyl-phosphane (100 mg, 329 mumol), potassium carbonate (568 mg, 4.11 mmol) and palladium(II) acetate (18.4 mg, 82.1 mumol) in THF (20.0 ml) and water (1.18 ml) was stirred at room temperature over night. The reaction mixture was diluted with water and extracted three times with EtOAc. The combined extracts were washed with water and brine, dried with Na2SO4 and concentrated in vacuo. The remaining residue was purified by chromatography (silica gel; DCM/EtOAc 100:0-90:10) and the title compound was obtained as colorless oil (385 mg, 58%). MS: 466.1 [M-H+OAc]-.

The chemical industry reduces the impact on the environment during synthesis Methyl 2-bromo-6-chlorobenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Aebi, Johannes; Binggeli, Alfred; Hertel, Cornelia; Konkar, Anish Ashok; Kuehne, Holger; Kuhn, Bernd; Maerki, Hans P.; Wang, Haiyan; US2012/165338; (2012); 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. 154825-97-5, name is Methyl 2-(4-bromophenyl)-2,2-dimethylacetate, A new synthetic method of this compound is introduced below., HPLC of Formula: C11H13BrO2

Preparation of Intermediate 1 -bromo-4-(1 -methoxy-2-methylpropan-2-yl)benzene (1AA- 11; Methyl 2-(4-bromophenyl)-2-methylpropanoate (23.5g, 86.6mmol) in tetrahydrofuran (175ml_) was cooled to -78C. Lithium aluminum hydride (100 ml. of 1.0 M solution) added slowly over 45 minutes and stirred for 3 hours at cold temperature. Reaction solution was slowly diluted with ethyl acetate and stirred for 10 minutes. 1 M hydrochloric acid was slowly added drop wise to reaction mixture. Diethyl ether (20OmL) added and layers separated. Organic washed with 1 M hydrochloric acid, brine, dried over sodium sulfate, filtered and concentrated to give 2-(4-bromophenyl)-2- methylpropan-1-ol (20m, 100%) as a white solid.

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; PFIZER INC.; ASPNES, Gary, Erik; DOW, Robert, Lee; MUNCHHOF, Michael, John; WO2010/86820; (2010); A1;,
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23877-12-5, Adding some certain compound to certain chemical reactions, such as: 23877-12-5, name is tert-Butyl 2-bromo-2-methylpropanoate, 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 23877-12-5.

2-Methyl-2-{4-[3-(4-trifluoromethyl-phenyl)-[1,2,4]thiadiazol-5-ylmethylsulfanyl]-phenoxy}-propionic acid tert-butyl ester To a three-necked flask containing NaH (36 mg, 0.90 mmol; 60% in mineral oil) was added a solution of B1 (220 mg, 0.598 mmol) in THF. To the mixture at 40 C. was added tert-butyl 2-bromoisobutyrate (287 mg, 1.29 mmol). After heating at 70 C. for 2 h, more tert-butyl 2-bromoisobutyrate (215 mg, 0.970 mmol) was added and the heating was continued overnight. The mixture was quenched with water (0.1 mL), concentrated, and chromatographed (EtOAc/hexane) to give 81 mg (27%) of B2; 1H NMR (300 MHz, CDCl3) delta 8.35 (d, J=8.2 Hz, 2 H), 7.71 (d, J=8.2 Hz, 2 H), 7.34 (d, J=8.8 Hz, 2 H), 6.78 (d, J=8.7 Hz, 2 H), 4.42 (s, 2 H), 1.55 (s, 6 H), 1.38 (s, 9 H); MS (ES) m/z: 511 (M+H+).

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 23877-12-5.

Reference:
Patent; Kuo, Gee-Hong; Shen, Lan; Wang, Aihua; Zhang, Yan; US2005/96362; (2005); 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 99548-54-6 as follows. 99548-54-6

A solution of methyl 3-bromo-2-methylbenzoate (from for example AstaTech, 24.35 g, 106 mmol) in benzene (300 mL) was treated with N-bromosuccinimide (22.7 g, 128 mmol) followed by benzoyl peroxide, 95% (1.3 g, 5.35 mmol). The reaction mixture was flushed with nitrogen and kept under nitrogen. The reaction mixture was heated at 80C for 2 days. The reaction mixture was concentrated under reduced pressure and treated with hexanes (200 mL). The resulting solids were filtered off, washed with hexanes then with 25% EtOAc / hexanes. The filtrate was concentrated under reduced pressure and the residue was absorbed directly onto silica gel. The product was purified by chromatography (ISCOCombiflash, 330 g, 200 ml/min, 0-8.7% EtOAc / Hexanes over 30 minutes) to yield the title compound (32.4 g, 105 mmol, 99% yield) as an orange liquid. LC/MS: RT= 1.13 min, m/z = 226.8/228.9.

According to the analysis of related databases, 99548-54-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; HARLING, John David; NEIPP, Christopher E.; PENDRAK, Israil; SMITH, Ian Edward David; TERRELL, Lamont Roscoe; YOUNGMAN, Mark; (120 pag.)WO2017/46036; (2017); 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. COA of Formula: C9H8F3NO2

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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