Category: esters-buliding-blocks

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. 40872-87-5, name is Methyl 3-amino-4-chlorobenzoate, This compound has unique chemical properties. The synthetic route is as follows., category: esters-buliding-blocks

2-Methoxy-4-methyl-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid (131 mg, 557 mumol) was suspended in DMF (1.70 mL). Methyl 3-amino-4-chlorobenzoate (155 mg, 835 mumol) was added, followed by triethylamine (283 mg, 390 muL, 2.8 mmol). HATU (318 mg, 835 mumol) was then added. Solution was initially clear but solid soon began to precipitate out of solution. After stirring at room temperature for 16 hours the reaction mixture was diluted with EtOAc (1 mL). The solid was then collected by filtration, washed with EtOAc and dried to give methyl 4-chloro-3-(2-methoxy-4-methyl-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidine-6-carboxamido)-benzoate. (Yield 108 mg, 244 mumol, 43.8%).

According to the analysis of related databases, 40872-87-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Anderson, Kevin; Chen, Yi; Chen, Zhi; Luk, Kin-Chun; Rossman, Pamela Loreen; Sun, Hongmao; Wovkulich, Peter Michael; US2012/184542; (2012); A1;,
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These common heterocyclic compound, 39149-80-9, name is tert-Butyl 2-bromopropanoate, 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. HPLC of Formula: C7H13BrO2

A.i. Rac-tert-butyl 2-(methylsulfonyl)propanoate:To a suspension of sodium methanesulfmate (15.63 g; 153 mmol) in tBuOH (50 mL) was added at rt and in one portion tert-butyl 2-bromopropionate (23.8 mL, 139 mmol). The mixture was refluxed overnight. The mixture was cooled down at rt and the solvent was removed under reduced pressure. The residue was taken up in EA (200 mL), filtered through Celite and the Celite was rinsed with EA (200 mL). The filtrate was concentrated to dryness to afford the title product as a white solid (28.4 g; 98% yield).1H NMR (d6-DMSO) delta: 4.24 (q, J = 7.2 Hz, 1H); 3.1 1 (s, 3H); 1.45 (s, 9H); 1.40 (d, J = 7.2 Hz, 3H).

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

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; GAUVIN, Jean-Christophe; SURIVET, Jean-Philippe; (136 pag.)WO2015/173329; (2015); A1;,
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Electric Literature of 22515-16-8, 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 22515-16-8 as follows.

General procedure: Solid, fine powdered lithiumaluminium hydride (2.0 – 5.0 equiv.) is suspended in dry THF at room temperature. The corresponding diacid- or diester derivative is dissolved in dry THF and the solution is slowly added dropwise to the lithiumaluminium slurry while cooling with an ice bath. After complete addition, the reaction solution is warmed to room temperature and the consumption of the starting material is checked by TLC. The suspension is carefully quenched with 2M H2SO4, additional water is added. For a better workup, the suspension should have a pH of ~7. The phases are separated and extracted with Et.20. The organic phase is washed with H2O, dried over MgSO4 and evaporated under reduced pressure. The crude product is directly used without further purification or purified via column chromatography using cyclohexane / tert. -butyl methyl ether. 1H NMR (500 MHz, CDCIs) delta 3.70 (t, 4H, J = 6.3 Hz), 2.00-1 .90 (m, 4H), 1 .79-1 .74 (m, 4H), 1 .38 (br s, 2H).

According to the analysis of related databases, 22515-16-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK PATENT GMBH; SCHRAUB, Martin; DOBELMANN-MARA, Lars; RIEDMUELLER, Stefan; (326 pag.)WO2018/149852; (2018); A1;,
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Related Products of 619-42-1, 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. 619-42-1, name is Methyl 4-bromobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A 50 mL round-bottomed flask, equipped with a gas inlet tube, a refluxcondenser and a magnetic stirring bar was charged with MCM-41-2PPdCl2 (102 mg, 0.05 mmol Pd), aryl halide (5.0 mmol) and HCOONa(7.5 mmol). The flask was flushed with CO. DMF (5 mL) was addedby syringe and a slow stream of CO was passed into the suspension.The mixture was vigorously stirred at 110-130 C for 2-20 h, cooledto room temperature and diluted with diethyl ether (50 mL). Thepalladium catalyst was separated from the mixture by filtration,washed with distilled water (2 × 10 mL), ethanol (2 × 10 mL) and ether(2 × 10 mL) and reused in the next run. The ethereal solution waswashed with water (3 × 20 mL), and dried over anhydrous magnesiumsulfate and concentrated under reduced pressure. The residue waspurified by flash column chromatography on silica gel (hexane-ethylacetate = 10 : 1).

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

Reference:
Article; Jiang, Jianwen; Wang, Pingping; Cai, Mingzhong; Journal of Chemical Research; vol. 38; 4; (2014); p. 218 – 222;,
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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. 14062-25-0, name is Ethyl 2-(4-bromophenyl)acetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: Ethyl 2-(4-bromophenyl)acetate

Step 1 :To a solution of ethyl 4-bromophenylacetate (4.5 g, 18.5 mmol) in 40 mL of DMF was added iodomethane (4.03 mL, 64.8 mmol) and sodium t-butoxide (4.45 g, 46.3 mmol). The resulting mixture was stirred at room temperature for 2 h. The reaction was quenched with water, and the mixture was extracted with EtOAc and hexane. The organic layer was separated and washed with saturated sodium bicarbonate solution. The organic layer was separated, dried over MgS04, and concentrated to give ethyl 2-(4-bromophenyl)-2-methylpropanoate (3.64 g, 73%).

The synthetic route of 14062-25-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHERING CORPORATION; SCOTT, Jack, D.; STAMFORD, Andrew, W.; GILBERT, Eric, J.; CUMMING, Jared, N.; ISERLOH, Ulrich; WANG, Lingyan; LI, Wei; WO2011/44187; (2011); A1;,
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Synthetic Route of 15963-46-9, These common heterocyclic compound, 15963-46-9, name is Methyl 3-chlorocyclobutanecarboxylate, 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 8-chloro-N-(4-chloro-2-hydroxyphenyl)-4-oxo-chromene-2-carboxamide (190 mg, 543 m mol), methyl 3-chlorocyclobutane-l-carboxylate (105 mg, 75 m L, 543 mmol) in DMF (5 mL) was added CS2CO3 (260 mg, 782 miho) at room temperature and the resulting mixture was then stirred at 90 C for 12 hours. After the reaction was completed, the mixture was diluted with water (30 mL) and extracted with EtOAc (50 mL) three times. The combined organic layer was washed with brine, dried over anhydrous Na2S04 and concentrated in vacuo to give methyl 3-(5-chloro-2-(8-chloro-4-oxo-chromene-2-carboxamido)phenoxy)cyclobutane- 1- carboxylate (200 mg, 79.8 %) as a yellow foam, which was used in next step directly without further purification. MS obsd. (ESL) [(M+H)+]: 462.1.

The synthetic route of 15963-46-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; FENG, Song; LIANG, Chungen; LIU, Yongfu; TAN, Xuefei; WU, Jun; WANG, Jianping; (134 pag.)WO2020/79106; (2020); 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. 18595-18-1, name is Methyl 3-amino-4-methylbenzoate, A new synthetic method of this compound is introduced below., Safety of Methyl 3-amino-4-methylbenzoate

2.47 g (34.5 mmol) of sodium nitrite was dissolved in 3.8 ml of water, and it was added dropwise to a mixture of 5.64 g (34.1 mmol) of methyl 3-amino-4-methyl-benzoate and 140 ml of acetic acid under ice-cooling. After the temperature of the reaction mixture was allowed to warm to room temperature and the mixture was stirred overnight, water was added to the mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and then dried over magnesium sulfate and filtered. The solvent was distilled off to give 4.83 g (yield: 80%) of methyl indazole-6-carboxylate. MASS(ESI+) m/z= 177 (M+H)+

The synthetic route of 18595-18-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nissan Chemical Industries, Ltd.; CHUGAI SEIYAKU KABUSHIKI KAISHA; EP2045253; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 13831-03-3,Some common heterocyclic compound, 13831-03-3, name is tert-Butyl propiolate, molecular formula is C7H10O2, 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.

Hexamethylphosphoric triamide (10.7 g, 59.9 mmol) was dissolved in tetrahydrofuran (160 mL) under nitrogen(0.5 M, 36 mL) was added at 0 C for 0.5 hour at 0 C, tert-butyl propiolate (5.04 g, 40 mmol) was added and the reaction was continued for 1 hour. Then add 2b (5.47g, 40mmol), gradually rose to room temperature, reaction 5 hours, slowly adding 1M hydrochloric acid to the reaction solution, adjust the reaction solution pH to 2 ~ 3, The organic phase was washed with saturated brine (100 mL x 1), dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography and purified. The organic phase was extracted with ethyl acetate (50 mL x 2) (Ethyl acetate: petroleum ether (v / v) = 0: 1 to 1: 9) to give the title compound 2c as a yellow oil (2.2 g, yield 21%).

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

Reference:
Patent; Sichuan Hai Sike Pharmaceutical Co., Ltd.; Wei Yonggang; Qiu Guanpeng; Lei Bolin; Li Yao; Wang Song; Zhu Guozhi; (39 pag.)CN106279128; (2017); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 884497-46-5, name is Methyl 3-amino-5-fluorobenzoate, 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 884497-46-5, Computed Properties of C8H8FNO2

Step C. Methyl 3-(dibenzylamino)-5-fluorobenzoate. To a solution of methyl 3-amino-5- fluorobenzoate (440 mg, 2.6 mmol) in dry DMF ( 10 mL) was added NaH ( 1 87 mg, 7.8 mmol) portionwise, followed by addition of benzyl bromide (1 . 1 g, 6.5 mmol). The reaction mixture was stirred at 40 C for 16 hr and concentrated. The resulting residue was purified by column chromatography to give the desired product. MS: 350 (M+ l )+.

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Reference:
Patent; AGIOS PHARMACEUTICALS, INC.; LEMIEUX, Rene M.; POPOVICI-MULLER, Janeta; TRAVINS, Jeremy M.; CAI, Zhenwei; CUI, Dawei; ZHOU, Ding; WO2015/10297; (2015); A1;,
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Application of 697762-67-7, 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. 697762-67-7, name is Methyl 5-bromo-2-chloro-3-methoxybenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 20 methyl 5-bromo-2-chloro-3-methoxybenzoate (25.0 g, 89.4 mmol) in 13 THF (100 mL), 21 H2O (100 mL) and MeOH (100 mL) was added aq. 5 N 26 NaOH solution dropwise at 0 C. The mixture was stirred at room temperature for 1 hour. 24 conc. HCl was added to the mixture to acidify and the mixture was extracted with EtOAc (500 mL×2). The combined organic layers were dried over MgSO4, filtered and concentrated in vacuo to afford the 27 title compound (22.6 g, 96%) as an orange solid. 1H NMR (400 MHz, CDCl3) delta 7.55 (s, 1H), 7.13 (s, 1H), 3.89 (s, 3H); [M+H]+ 265.

The synthetic route of Methyl 5-bromo-2-chloro-3-methoxybenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DAEWOONG PHARMACEUTICAL CO., LTD.; GREEN CROSS CORPORATION; YOON, Hee-kyoon; PARK, Se-Hwan; YOON, Ji-Sung; CHOI, Soongyu; SEO, Hee Jeong; PARK, Eun-Jung; KONG, Younggyu; SONG, Kwang-Seop; KIM, Min Ju; PARK, So Ok; (55 pag.)US2019/169174; (2019); A1;,
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Ester – an overview | ScienceDirect Topics