Month: July 2021

Application of 14062-24-9, 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. 14062-24-9, name is Ethyl 4-chlorophenylacetate, This compound has unique chemical properties. The synthetic route is as follows.

Ethyl alpha-[[(2-chloro-4-pyridinyl)amino]methylene]-(4-chlorophenyl)acetate. A solution of ethyl (4-chlorophenyl)acetate (10.87 g, 54.72 mmol) in 90 mL of ethyl formate was treated with a 60% suspension of NaH in oil (7.0 g, 175 mmol) added in portions. After stirring overnight, the reaction was added to 130 mL of 10% aq. HCl and 70 mL of water. The resulting mixture was extracted with EtOAc (3×50 mL). The pooled EtOAc layers were washed with water and brine, dried (Na2SO4), filtered and concentrated. The residue was treated with solid 4-amino-2-chloropyridine (7.08 g) and 100 mL of EtOH. After 48 h at reflux, the reaction was allowed to cool to room temperature. After standing overnight, the precipitate that formed by isolated and washed with EtOH, affording 8.0 g of the desired product

The chemical industry reduces the impact on the environment during synthesis Ethyl 4-chlorophenylacetate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Kanner, Richard; US2010/190819; (2010); 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. 98545-64-3, name is Methyl 4-amino-2-bromobenzoate, A new synthetic method of this compound is introduced below., Quality Control of Methyl 4-amino-2-bromobenzoate

A solution of methyl 2-bromo-4-amino benzoate (3 g, 13 mmol) and triethylamine (2.5 ml, 18 mmol) in dichloromethane (50 ml) was cooled to 0 and was treated with a slurry of 2-(pyridin-2-yl)benzoyl chloride in dichloromethane (20 ml). Stirring at room temperature was maintained for 4 hours. The reaction was quenched with 20% acetic acid, wash sequentially with saturated aqueous sodium bicarbonate, water then saturated brine solution. The solution was dried (MgSO4), filtered and concentrated in vacuo to give 5.23 g of a white foam. MS (+FAB) m/z 411/413 (M+H)+. Analysis for: C20H15BrN2O3 Calcd: C, 58.41; H, 3.68; N, 6.81. Found: C, 57.73; H, 3.66; N, 6.54

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; Wyeth; EP1021444; (2003); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 82702-31-6, 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. 82702-31-6, name is Methyl 3-bromo-4-fluorobenzoate, This compound has unique chemical properties. The synthetic route is as follows.

Potassium carbonate (681 mg, 4.93 mmol) was added to 2-chloro-4-cyclopropyl-6-methylphenol (300 mg, 1.64 mmol) and methyl 3-bromo-4-fluorobenzoate (363 mg, 1.56 mmol) ) in a solution of dimethyl sulfoxide (10 mL). The reaction solution was reacted at 80 C for 5 hours under a nitrogen atmosphere. The reaction solution was cooled and added to water (25 mL). Ethyl acetate extraction (25 mL * 2), the organic phase was dried and evaporated to dryness to give a crude product, the crude product was separated by column ( petroleum ether: ethyl acetate = 20:1) Methyl 3-bromo-4-(2-chloro-4-cyclopropyl-6-methylphenoxy)benzoate (500 mg, yield 77%).

The chemical industry reduces the impact on the environment during synthesis Methyl 3-bromo-4-fluorobenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Shanghai Hansen Bio-pharmaceutical Technology Co., Ltd.; Jiangsu Haosen Pharmaceutical Group Co., Ltd.; Ye Guozhong; Liu Lei; Bao Rudi; Wu Shenghua; Deng Haining; (130 pag.)CN110041253; (2019); A;,
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. 260352-79-2, name is Butyl 2,2-difluorocyclopropanecarboxylate, This compound has unique chemical properties. The synthetic route is as follows., Formula: C8H12F2O2

Referential Example 2 5-(2,2-Difluorocyclopropyl)-lH-pyrazol-3-amine (45) To a solution of MeCN (1.1 g, 16.8 mmol) in THF (60 mL) was added dropwise n-BuLi in THF (11.2 mL, 40.3 mmol) at -78C, and the reaction mixture was stirred at -78 C under N2 for 30 min. Butyl 2,2- difluorocyclopropanecarboxylate (3.0 g, 16.8 mmol) was added at -78 C, and the reaction mixture was allowed to warm to RT over 3 h. The reaction mixture was quenched with water and adjusted to pH 7 with IN HCl. The mixture was extracted with EtOAc, and the organic layer was washed with brine, dried (Na2S04), filtered and concentrated in vacuo to afford crude 3-(2,2-difluorocyclopropyl)-3- oxopropanenitrile. A mixture of crude 3-(2,2-difluorocyclopropyl)-3-oxopropanenitrile and hydrazine (2.0 g, 50.4 mmol, 85% pure) in EtOH (30 mL) was stirred at reflux for 16 h. The reaction mixture was concentrated to dryness under reduced pressure. The crude residue was purified by chromatography eluting with an EtO Ac/petroleum ether gradient (12.5 to 100% EtOAc) to afford 2.1 g (78.5%>) of 45 as a yellow solid: 1H NMR (400 MHz, DMSO-d6): delta 11.40 (br s, 1H), 5.26 (s, 1H), 4.80 (br s, 2H), 2.78 – 2.66 (m, 1H), 2.04 – 1.75 (m, 1H), 1.73 – 1.21 (m, 1H); MS (ESI+) m/z = 160.1 [M +1]+.

According to the analysis of related databases, 260352-79-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; ALIAGAS-MARTIN, Ignacio; CRAWFORD, James; LEE, Wendy; MATHIEU, Simon; RUDOLPH, Joachim; WO2013/26914; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 924-99-2, A common heterocyclic compound, 924-99-2, name is Ethyl 3-(dimethylamino)acrylate, molecular formula is C7H13NO2, 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: Ethyl 4-(4-chlorophenyl)-2-thioxo-1,2,3,4-tertahydropyrimidine-5-carboxylate 6a (Table 2, entry 1). To a mixture of thiourea 12a (23.0 mg, 0.302 mmol), 4-chlorobenzaldehyde 13a (63.0 mg, 0.448 mmol), and ethyl 3-dimethylaminoacrylate 9 (64.0 mg, 0.447 mmol) in anhydrous DMF (0.3 mL) was added anhydrous aluminum chloride (8.0 mg, 0.0600 mmol) at room temperature, and the reaction mixture was stirred at 110 C for 3 h. To the mixture was added EtOAc (10 mL) and 1 M HCl aqueous solution (5 mL), and the organic layer was separated. The aqueous layer was extracted with EtOAc (10 mL), and the combined organic layers were washed with water (5 mL) and brine (5 mL), dried over anhydrous MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography [n-hexane-EtOAc (4:1 to 2:1)] to give 6a (78.9 mg, 0.266 mmol, 88%) as pale yellow crystals.

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; Arai, Rie; Cho, Hidetsura; Gokurakuji, Yuki; Kikuchi, Hidetomo; Kubo, Takanori; Nakamura, Yuri; Nishimura, Yoshio; Sunaga, Katsuyoshi; Yuan, Bo; Tetrahedron Letters; (2020);,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 83881-47-4,Some common heterocyclic compound, 83881-47-4, name is Methyl 2-(2-chloroethoxy)acetate, molecular formula is C5H9ClO3, 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.

11. Levorotatory dimaleate of methyl 2-[2-[4-[(4-chlorophenyl)phenylmethyl ]-1-piperazinyl]ethoxy]acetate. 46 g (0.16 mole) of levorotatory (-)-1-[(4-chlorophenyl)phenylmethyl]piperazine (prepared in Example 4.1), 36.6 g (0.24 mole) of methyl (2-chloroethoxy)acetate, 37.3 g (0.35 mole) of anhydrous sodium carbonate and 1.05 g(0.0064 mole) of potassium iodide are suspended in 46 ml of toluene. The suspension is heated with stirring for 18 hours at reflux temperature, then cooled to ambient temperature and filtered. The solids are washed with 100 ml of toluene and the filtrate and the washing solvent are combined. The toluene is evaporated at 50 C. under reduced pressure in a rotating evaporator. 76 g of a brown oil are obtained and are taken up in 80 ml of dichloromethane. The solution is purified by chromatography (silica column (15 to 40 mum) 1 kg; eluent: pure dichloromethane gradually diluted with methanol up to a maximum of 2% of methanol (v/v)). 43.5 g of methyl 2-[2-[ 4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]ethoxy]acetate in the form of an oil are thus obtained. Yield: 67.5%.

The synthetic route of 83881-47-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; U C B, S.A.; US5478941; (1995); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

251458-15-8, name is Methyl 2-(3-bromophenyl)-2-methylpropanoate, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. HPLC of Formula: C11H13BrO2

To a solution of ferf-butyl (4-(4,4,5,5-tetramethyl-1.3,2-dioxaborolan-2-yl)benzyl)carbamate (1.46 g, 4.40 mmol) in 1 .4-dioxane (20 mL) and water (2 mL) was added methyl 2-(3-bromo- phenyl)-2-methylpropanoate (1.13 g, 4.40 mmol), Na2C03(1.20 g, 8.80 mmol) and Pd(dppf)CI2(150 mg) and the mixture was stirred at 90C for 3 h under N2, cooled, diluted with water (40 mL) and extracted with EA (3 x 20 mL). The combined organic layer was washed with brine (30 mL), dried over Na2S04, filtered, concentrated and purified by FCC (PE:EA = 10: 1 ) to give compound 24a as a white solid.

The synthetic route of 251458-15-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHENEX-FXR GMBH; GEGE, Christian; BIRKEL, Manfred; HAMBRUCH, Eva; DEUSCHLE, Ulrich; KREMOSER, Claus; (203 pag.)WO2019/16269; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 5445-17-0, name is Methyl 2-bromopropanoate, 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 5445-17-0, Recommanded Product: Methyl 2-bromopropanoate

A solution of 1-(5-trifluoromethyl-pyridin-2-yl)-piperazine (0.9 g, 3.9 mmoles) in MeOH (13 mL) and DIPEA (1.5 mL) was treated with 2-bromo-propionic acid methyl ester (0.48 mL, 4.3 mmoles) and stirred overnight at 70 C. MeOH was removed under reduced pressure and the residue was purified (silica gel, 10-40% acetone in hexane) to provide the title compound as a yellowish solid (1.23 g, 99%).

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

Reference:
Patent; Hoff, Ethan D.; Link, James T.; Pliushchev, Marina A.; Rohde, Jeffrey J.; Winn, Martin; US2005/245532; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 4630-80-2,Some common heterocyclic compound, 4630-80-2, name is Methyl cyclopentanecarboxylate, molecular formula is C7H12O2, 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 168 Preparation of 1-(4-Bromobutyl)cyclopentane Carboxylic Acid Methyl Ester To a solution of diisopropylamine (150 mmol, 21 mL) in THF (100 mL) was added dropwise a solution of n-butyl lithium (145 mmol, 58 mL, 2.5M) in hexanes at -10 C. while maintaining the temperature below 0 C. After addition, the solution was stirred for 30 min at 0 C. To this a solution of methyl cyclopentane carboxylate (100 mmol, 13.1 g) in THF (20 mL) was added dropwise at -70 C. maintaining the internal temperature between -60 to -70 C. After addition, the reaction mixture was stirred for 1 h at -50 to -60 C. Then, a solution of 1,4-dibromobutane (100 mmol, 21.59 g) in THF (20 mL) was added dropwise and the light brown suspension was stirred for 1 h at -60 to -70 C. Then, it was allowed to warm to room temperature and stirred overnight. The reaction mixture was poured into a saturated solution of ammonium chloride (200 mL) and the organic compound was extracted into ether (2*100 mL). The combined extracts were washed with a saturated brine solution (150 mL) and dried over anhydrous magnesium sulfate. After filtration of the drying agent, the solution was concentrated under vacuum and the resulting residue was distilled at 120-133 C./2.5 mm Hg to obtain 1-(4-bromobutyl)cyclopentane carboxylic acid methyl ester as a colorless oil (12.8 g, 48%). HR MS (C11H19BrO2): Obs mass, a 262.0565. Calcd mass, 262.0568 (M+).

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

Reference:
Patent; Hoffmann-La Roche Inc.; US6455550; (2002); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 94994-25-9, A common heterocyclic compound, 94994-25-9, name is Methyl 4-formylbicyclo[2.2.2]octane-1-carboxylate, molecular formula is C11H16O3, 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.

Intermediate A51M: Methyl 4-(difluoromethyl)bicyclo[2.2.2]octane-1-carboxylate To a solution of Intermediate A51L (400 mg, 2.038 mmol) at 0 C. in CH2Cl2 (8 mL) was added DAST (0.673 mL, 5.10 mmol). The reaction mixture was stirred at RT overnight. The reaction mixture was cooled to 0 C. and carefully quenched with a solution of NaHCO3. The layers were separated. The aqueous layer was extracted with CH2Cl2. The combined organic layer was washed with brine, dried over Na2SO4, and filtered. The filtrate was concentrated. The residue was purified by silica gel chromatography (40 g REDISEP column, eluting with 0-20% EtOAc in hexane). Fractions containing the product were combined and evaporated to afford Intermediate A51M (280 mg, 62.9%). MS(ES): m/z=199 [M+H]+; 1H NMR (400 MHz, chloroform-d) delta ppm 5.54-5.26 (m, 1H), 3.68 (s, 3H), 1.89-1.76 (m, 6H), 1.65-1.50 (m, 6H).

The synthetic route of 94994-25-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bristol-Myers Squibb Company; Velaparthi, Upender; Darne, Chetan Padmakar; Liu, Peiying; Wittman, Mark D.; Pearce, Bradley C.; Araujo, Erika M. V.; Dasgupta, Bireshwar; Nair, Jalathi Surendran; Janakiraman, Sakthi Kumaran; Rachamreddy, Chandrasekhar Reddy; Rao, Mettu Mallikarjuna; Karuppiah, Arul Mozhi Selvan Subbiah; Reddy, Bandreddy Subba; Nagalakshmi, Pulicharla; Bora, Rajesh Onkardas; Maheshwarappa, Shilpa Holehatti; Kumaravel, Selvakumar; Mullick, Dibakar; Sistla, Ramesh; (353 pag.)US9273058; (2016); B2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics