Month: March 2021

41841-16-1, name is Methyl 2-(4-bromophenyl)acetate, 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: C9H9BrO2

To a suspension of sodium hydride (60% in oil, 192 mg, 4.80 mmol,) in DMF (11 mL) at 0 C was added methyl 2-(4-bromophenyl)acetate (0.35 mL, 2.2 mmol). The mixture was stirred for 15 minutes at 0 C and iodomethane (6.5 muL¡¤, 0.10 mmol) was added. The mixture was stirred for further 5 minutes at 0 C and at RT for 12 h, then quenched with 1 N aq. HCl (1 mL) and extracted with EtOAc (3 x 2 mL). The organic layer washed with H20 (3 x 2 mL) and brine (2 mL), dried over Na2S04, filtered and concentrated under reduced pressure. The residue was purified by Si02gel chromatography (0% to 5% EtOAc/Hexanes) to give methyl 2-(4- bromophenyl)-2-methylpropanoate (550 mg, 98%); MS (ES+) CgHgBrC^ requires: 228, found: 229/231 [M+H]+.

The synthetic route of 41841-16-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JONES, Philip; DIFRANCESCO, Maria, Emilia; PETROCCHI, Alessia; MARSZALEK, Joe; LIU, Gang; KANG, Zhijun; CARROLL, Christopher, L.; MCAFOOS, Timothy; CZAKO, Barbara; WO2014/31928; (2014); A2;,
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Adding a certain compound to certain chemical reactions, such as: 106896-49-5, name is Methyl 4-amino-3-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 106896-49-5, Computed Properties of C8H8BrNO2

To a 1 L round-bottom flask, purged and maintained under an inert atmosphere of nitrogen, was added methyl 4-amino-3-bromobenzoate A-7a (25 g, 108.67 mmol , 1.0 equiv.), K3PO4 (65 g, 306.21 mmol, 2.82 equiv.), toluene (50 mL), water (100 mL), P(Cy)s (2.8 g, 0.05 equiv.), Pd(OAc)2 (2.25 g, 10.02 mmol, 0.09 equiv.), and cyclopropyl boronic acid (26 g, 302.69 mmol, 2.79 equiv.). The resulting mixture was heated at 100 C overnight. The resulting solids were removed by filtration. The filtrate was diluted with H2O (200 mL) and extracted with ethyl acetate (200 mL x 3). The combined organic layers were concentrated in vacuo and the resulting residue was purified via silica gel column chromatography eluting with EtOAc PE (1 :20 to 1 : 10 and to 1 :5) to provide methyl 4-amino-3-cyclopropylbenzoate A-7b (19.9 g, 96%) as a light brown 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, Methyl 4-amino-3-bromobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARDELYX, INC.; CHAO, Jianhua; JAIN, Rakesh; HU, Lily; LEWIS, Jason Gustaf; BARIBAULT, Helene; CALDWELL, Jeremy; (249 pag.)WO2018/39384; (2018); A1;,
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Electric Literature of 4897-84-1, A common heterocyclic compound, 4897-84-1, name is Methyl 4-bromobutanoate, molecular formula is C5H9BrO2, 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 solution of the methyl ester (XIV, 1.8 g, 0.15 mmol) in DMF (50 mL), is added 4-bromo-butyric acid methyl ester (1 g, 0.87 mmol) and Cs2CO3 (800 mg, 0.48 mmol). The reaction is stirred at 22¡ã C. for 48 hours. 5 g SiO2 is added to the mixture and all solvents were evaporated in vacuo. The solid is purified by flash chromatography, eluting with MeOH/DCM (0-10percent) to provide 1.5 g (75percent), of a yellow solid. MS m/z 1357 (M +H2O).

The synthetic route of 4897-84-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bushell, Simon; LaMarche, Matthew J.; Leeds, Jennifer; Whitehead, Lewis; US2009/156628; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 4891-38-7, name is Methyl Phenylpropiolate, 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 4891-38-7, category: esters-buliding-blocks

The reaction was carried out in a 10 ml Schlenk reaction tube. The reaction tube was evacuated and replaced with argon three times. 5 mol % (6.1 mg) of [Cp*RuCl2]2 (relative to substrate 1b) and 2 ml of solvent 1,2- were added. Dichloroethane, stirring 2min;Then 0.2 mmol (48.6 mg) of aziridine 1b and 1.0 mmol (160.2 mg) of methyl phenylpropiolate 2a are added and the reaction is heatedStir for 20 hours at 80C.After the reaction is completed, the solvent is removed by a rotary evaporator, and the solid is dissolved in dichloromethane and subjected to silica gel column chromatography using petroleum ether:The column was washed with an eluent of ethyl acetate = 10:1 – 5:1 (by volume) to give 46.8 mg of a white solid polysubstituted pyrrole compound 3b in an isolated yield of 58%.

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 Phenylpropiolate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Dalian Institute of Chemical Physics; Wan Boshun; Li Tengfei; Wu Fan; (17 pag.)CN107522645; (2017); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 3618-04-0,Some common heterocyclic compound, 3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate, molecular formula is C9H16O3, 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 B Ethyl 4-oxocyclohexanecarboxylate Ethyl 4-hydroxybenzoate is reduced to ethyl 4-hydroxycyclohexanecarboxylate according to the procedure described in R. A. Finnegan and P. L. Bachman, Journal of Organic Chemistry, Volume 30, pages 4145-4150 (1965). The crude material obtained in this reduction (190 g) is dissolved in 1200 ml of reagent grade acetone. The solution is cooled to 0 C. and 152 ml of a 8 N chromic acid solution (prepared from concentrated sulfuric acid and chromium trioxide) is added dropwise to the mechanically stirred reaction mixture. Enough isopropanol is added to the mixture to discharge its red color and it is then filtered through Celite. The salts are washed with several portions of acetone. The filtrate is evaporated in vacuo. The residue is dissolved in 750 ml of diethyl ether and washed with sodium bicarbonate and brine solutions. After drying, the solvent is evaporated and the residue is distilled to yield the title compound; bp12 125 C. In a process analogous to Example B using appropriate starting materials the following compound is prepared:

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route trans-Ethyl 4-hydroxycyclohexanecarboxylate, its application will become more common.

Reference:
Patent; Warner-Lambert Company; US4988699; (1991); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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 51760-21-5 as follows. COA of Formula: C10H9BrO4

StepA: Pd0 couplingTo a solution of dimethyl 5-bromo-isophthalate (5.75 g, 21.1 mmol) in THF (50 ml) was added 2- cyanophenylzinc bromide (50.5 ml, 25.3 mmol) followed by tetrakis(triphenylphosphine)palladium (0) (0.122 g, 0.105 mmol). The solution was stirred overnight at 50 C. The next day the solution was cooled, filtered, and concentrated in vacuo. Purification by flash chromatography on silica gel (25% EtOAc in Hexanes) afforded 3.8g. lH NMR (400 MHz, CDCI3) delta 8.41 (d, J = 1.6 Hz, 1H), 7.85-7.80

According to the analysis of related databases, 51760-21-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK & CO., INC.; WO2006/55434; (2006); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 27798-60-3,Some common heterocyclic compound, 27798-60-3, name is Methyl 2-Methoxyphenylacetate, molecular formula is C10H12O3, 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.

Preparation of methyl 2-(2-methoxyphenyl)-3-phenylpropanoate (27): A 50OmL round- bottom flask is charged with methyl 2-(2-methoxyphenyl)acetate (8.496 g, 47 mmol, leq) and THF (20OmL). The homogeneous mixture is cooled to 0 0C in an ice bath. Lithium diisopropyl amide (23.5mL of a 2.0M solution in heptane/THF) is added, maintaining a temperature less than 30C. The reaction is stirred 45 minutes at this reduced temperature. Benzyl bromide (5.6mL, 47mmol, leq) is added dropwise. The reaction is allowed to gradually warm to roomtemperature and is stirred for 18 hours. The reaction is quenched with IN HCl and extracted 3 times with equal portions of EtOAc. The combined extracts are washed with H2O and brine, dried over Na2SO4, filtered, and concentrated. The residue is purified over silica to afford 4.433g (35%) of the desired compound. ESI+ MS 293 (M+Na).

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-Methoxyphenylacetate, its application will become more common.

Reference:
Patent; AKEBIA THERAPEUTICS INC.; SHALWITZ, Robert; WO2011/5330; (2011); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 28868-76-0, These common heterocyclic compound, 28868-76-0, name is Dimethyl 2-chloromalonate, 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.

b) 18.2 g of 2-chloro-5-methoxyphenol were dissolved in 150 ml of dry methanol. 9.3 g of MeONa were added, followed by 25 g of dimethyl chloromalonate. 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 (2-chloro-5-methoxy)phenoxy-dimethylmalonate, white crystals with m.p. 68-69 C.

Statistics shows that Dimethyl 2-chloromalonate is playing an increasingly important role. we look forward to future research findings about 28868-76-0.

Reference:
Patent; Hoffmann-La Roche Inc.; US5837708; (1998); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 1504965-88-1, 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. 1504965-88-1, name is Methyl 5-amino-2-fluoro-4-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of methyl 5-amino-2-fluoro-4-methyl-benzoate (500 mg, 2.73 mmol) in methanol (3 mL) was added ammonia (2 mL of 7 M, 14 mmol), and the mixture was stirred for 16 hours at room temperature. Additional ammonia (2 mL of 7 M, 14 mmol) was added and the reaction was stirred for 6 hours. The reaction mixture was concentrated in vacuo to afford 5-amino-2-fluoro-4-methyl- benzamide (390 mg, 85%) as a yellow solid. ESI-MS m/z calc. 168.07, found 169.0 (M+l)+; retention time (Method F): 0.42 minutes (1.5 minute run).

The chemical industry reduces the impact on the environment during synthesis Methyl 5-amino-2-fluoro-4-methylbenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; AHMAD, Nadia; ANDERSON, Corey; ARUMUGAM, Vijayalaksmi; ASGIAN, Iuliana, Luci; CAMP, Joanne, Louise; FANNING, Lev Tyler, Dewey; HADIDA RUAH, Sara, Sabina; HURLEY, Dennis; SCHMIDT, Yvonne; SHAW, David; SHETH, Urvi, Jagdishbhai; THOMSON, Stephen, Andrew; (691 pag.)WO2019/14352; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 89-71-4, name is Methyl 2-methylbenzoate, 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. COA of Formula: C9H10O2

To a mixture of methyl 2-methylbenzoate (5.0 g, 0.033 mmol) and N- bromosuccinimide (5.9 g, 0.033 mmol) in CCU (50 ml_) was added benzoyl peroxide (0.04 g, 0.00016 mmol). The mixture was heated to reflux for 1.5 h, cooled to room temperature, filtered through Celite, and concentrated to afford methyl 2- (bromomethyl)benzoate (7.2 g, ca. 94% mass recovery), which was contaminated with ca. 14% unreacted starting material and was used without purification.

The synthetic route of Methyl 2-methylbenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WYETH; WO2006/128142; (2006); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics