Category: esters-buliding-blocks

106614-28-2, name is Methyl 2,4-difluorobenzoate, 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. SDS of cas: 106614-28-2

Example 3H methyl 2-(1H-pyrrolo[2,3-b]pyridin-5-yloxy)-4-fluorobenzoate A mixture of EXAMPLE 3G (8.5 g), methyl 2,4-difluorobenzoate (7.05 g), and K3PO4 (9.32 g) in diglyme (40 mL) at 115 C. was stirred for 24 hours. The reaction was cooled, diluted with ether (600 mL), and washed twice with water, and brine, and concentrated. The crude product was chromatographed on silica gel with 2-50% ethyl acetate/hexanes.

The synthetic route of 106614-28-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBOTT LABORATORIES; US2010/305122; (2010); A1;,
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46064-79-3, name is Methyl 3-amino-4-bromobenzoate, 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. COA of Formula: C8H8BrNO2

Benzoyl isothiocyanate (3.12 g, 19.1 mmol) was added to a stirred mixture ofmethyl 3-amino-4-bromobenzoate (4.0 g, 17.4 mmol) in acetone (40 ml) and the mixture was stirred at 60C for 6 hr. After being cooled to room temperature, the reaction mixture was evaporated under vacuum. The residue was purified by column chromatography on silica gel Isolute Flash Si; 50 g prepacked, eluted with EA/PE (0-30%) to give the title compound: LCMS (ESI) calc?d for C,6H,3BrN2O3S [M + H]: 393, 395 (1:1), found 393, 395 (1:1); ?H NMR (400 MHz, DMSO-d6): oe12.65 (s, 1H), 11.91 (s, 1H), 8.47 (d, J= 2.0 Hz, 1H), 8.02-8.00 (m, 2H), 7.92-7.91 (m, 1H), 7.81-7.80 (m, 1H), 7.78-7.69 (m, 1H), 7.58-7.54 (m, 2H), 3.88 (s, 3H).

The synthetic route of 46064-79-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BENNETT, Frank; JIANG, Jinlong; PASTERNAK, Alexander; DONG, Shuzhi; GU, Xin; SCOTT, Jack D.; TANG, Haiqun; ZHAO, Zhiqiang; HUANG, Yuhua; HUNTER, David; YANG, Dexi; ZHANG, Zhibo; FU, Jianmin; BAI, Yunfeng; ZHENG, Zhixiang; ZHANG, Xu; YOUNG, Katherine; XIAO, Li; (580 pag.)WO2016/206101; (2016); A1;,
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These common heterocyclic compound, 3044-06-2, name is Diethyl 2-(1-ethoxyethylidene)malonate, 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. Application In Synthesis of Diethyl 2-(1-ethoxyethylidene)malonate

Reference Example 196 Ethyl 4-hydroxy-6-methylpyrimidine-5-carboxylate A mixture of diethyl malonate (4.8 mL), triethyl orthoacetate (17 mL), acetic anhydride (0.11 mL) and zinc chloride (1.2 g) was stirred at 140C. To the mixture was added acetic anhydride (0.11 mL) each after 30, 90 and 120 minutes, and then stirred at the same temperature overnight. The reaction mixture was cooled to room temperature, and the insoluble material was removed by filtration. The filtrate was concentrated under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate = 4/1 – 7/3) to give diethyl 2-(1-ethoxyethylidene)malonate (5.02 g). To a solution of diethyl 2-(1-ethoxyethylidene)malonate (4.13 g) in ethanol (15 mL) were added formamidine hydrochloride (1.73 g) and a solution of potassium hydroxide (2.21 g) in water (7.5 mL), and the mixture was stirred at room temperature for 2 days. The reaction mixture was neutralized by adding acetic acid. To the mixture was added ethyl acetate (30 mL), and the mixture was stirred at room temperature for 30 minutes. The insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate – ethyl acetate/methanol = 9/1) to give the title compound (1.5 g).

The synthetic route of Diethyl 2-(1-ethoxyethylidene)malonate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kissei Pharmaceutical Co., Ltd.; EP2143724; (2010); A1;,
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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. 39149-80-9, name is tert-Butyl 2-bromopropanoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: tert-Butyl 2-bromopropanoate

To a suspension of sodium methanesulfinate (100 g; 929 mmol) in tBuOH (350 mL) was added tert-butyl-2-bromopropionate (150 mL; 877 mmol). The reaction mixture was stirred at about 90C for 24 h under nitrogen atmosphere, then cooled to rt and concentrated to dryness. The residue was partitioned between water (750 mL) and EA (600 mL). The aq. layer was extracted with EA (2 x 500 mL). The evaporation residue afford the title compound as a white yellow solid (175 g, 96% 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 39149-80-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; CHAPOUX, Gaelle; DIETHELM, Stefan; GAUVIN, Jean-Christophe; PANCHAUD, Philippe; SURIVET, Jean-Philippe; (90 pag.)WO2017/37039; (2017); A1;,
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Reference of 27492-84-8, These common heterocyclic compound, 27492-84-8, name is Methyl 4-amino-2-methoxybenzoate, 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 methyl 4-amino-2-methoxybenzoate 5 (2.00 g, 11.0 mmol, 1 eq.) in MeCN (70 mL) was added N-iodosuccinimide (5.22 g, 23.2 mmol, 2.1 eq.) in 2 portions over 5 minutes. The resulting mixture was stirred at rt under argon for 1h, then at 55°C. N-iodosuccinimide (1.0 eq.) was added every 5h until completion of the reaction. The reaction mixture was then partitioned between CHCl3 and sat. aq. NaHCO3. A small amount of sat. aq. Na2S2O3 was added to quench potential traces of iodine. The aqueous phase was extracted 3 times. The combined organic phases were dried (MgSO4) and concentrated under reduced pressure. The product (2.10 g, 44percent) was obtained after purification by flash column chromatography (hexane/AcOEt 8:2). Rf 0.4 (hexane/AcOEt, 8:2); 1H NMR (400 MHz, CDCl3) delta 3.85 (s, 3H), 3.88 (s, 3H), 5.15 (br. s., 2H), 8.27 (s, 1H); 13C NMR (100 MHz, CDCl3) delta 52.1, 61.9, 74.0, 81.5, 114.7, 142.4, 151.2, 161.6, 163.7; HRMS (ESI+) m/z calcd for C9H10I2NO3 [M + H]+ 433.8745, found: 433.8746.

Statistics shows that Methyl 4-amino-2-methoxybenzoate is playing an increasingly important role. we look forward to future research findings about 27492-84-8.

Reference:
Article; Baud, Matthias G.J.; Bauer, Matthias R.; Verduci, Lorena; Dingler, Felix A.; Patel, Ketan J.; Horil Roy, Deeptee; Joerger, Andreas C.; Fersht, Alan R.; European Journal of Medicinal Chemistry; vol. 152; (2018); p. 101 – 114;,
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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., Safety of Methyl 2-bromo-6-chlorobenzoate

To a solution of methyl 2-bromo-6-chlorobenzoate (7.50 g, 30.1 mmol) in dioxane (65 mL) was added BPD (15.3 g, 60.3 mmol), AcOK (3.54 g, 36.1 mmol) and PdCl2(dppf) (0.66 g, 0.90 mmol) under N2 atmosphere, then the resulting mixture was stirred at 100 C. for 18 h, cooled to room temperature, filtered and concentrated, and the residue was purified by chromatography (0-3% EtOAc in petroleum ether) to give the title compound. MS: 297 (M+1). 1H NMR (400 MHz, CDCl3) delta 7.67 (d, J=7.4 Hz, 1H), 7.46 (d, J=7.8 Hz, 1H), 7.29-7.39 (m, 1H), 3.92 (s, 3H), 1.32 (s, 12H).

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 685892-23-3.

Reference:
Patent; Merck Sharp & Dohme Corp.; Lapointe, Blair T.; Fuller, Peter H.; Gunaydin, Hakan; Liu, Kun; Molinari, Danielle F.; Pu, Qinglin; Scott, Mark E.; Trotter, B. Wesley; Zhang, Hongjun; US2018/305320; (2018); 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 1236357-65-5 as follows. Product Details of 1236357-65-5

To degassed toluene (25 mL) was added palladium acetate (18 mg, 0.0825 mmol) and Xphos (79 mg, 0.165 mmol) and the mixture was degassed a further 30 minutes. To this reaction mixture was added methyl 1-(4-bromophenyl)cyclobutanecarboxylate (900 mg, 3.3 mmol) and cesium carbonate (3.2 g, 9.9 mmol) and this was degassed for a further 10 minutes. Beta-alanine ethyl ester (920 mg, 6.6 mmol) and diisopropylethyl amine (1.1 ml, 6.6 mmol) were added and this was brought to reflux and stirred overnight. The reaction was cooled to room temperature and poured onto water (100 ml). It was then extracted with ethyl acetate (2*100 ml), dried over magnesium sulfate, filtered, and evaporated to give methyl 1-(4-(3-ethoxy-3-oxopropylamino)phenyl)cyclobutanecarboxylate. Taken on crude to the next reaction. 1H NMR (400 MHz, CDCl3) 7.1 (d, 2H), 6.55 (d, 2H), 4.15 (m, 2H), 3.65 (s, 3H), 3.45 (m, 2H), 2.75 (m, 2H), 2.60 (t, 2H), 2.45 (m, 2H), 1.95 (m, 1H), 1.85 (m, 1H), 1.35 (m, 3H)

According to the analysis of related databases, 1236357-65-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; pfizer Inc; US2010/197591; (2010); A1;,
Ester – Wikipedia,
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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. 2005-10-9, name is 6H-Benzo[c]chromen-6-one, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 6H-Benzo[c]chromen-6-one

2a (58.8 mg, 0.3 mmol) and MeCN (3 mL) was added to a flask (10 mL), then NaOH aqueous solution (5% (W/W), 2 mL) was dropped. After stired for 3 h at room temperature, the reaction mixture was wished with CH2Cl2 (3 5 mL) and filtered through Celite. After evaporation of the solvent under vacuum, the residue was purified by column chromatography on silica gel (100-200 mesh) using petroleum ether-EtOAc (10/1, V/V) as eluent to give pure 5. 4.3.35. 20-Hydroxy-(1,10-biphenyl)-2-carboxylic acid (5) Prepared from 6H-benzo[c]chromen-6-one; isolated as white solid (63.0 mg, 98%), m.p. 90-91 C (lit.25 93 C); 1H NMR(500 MHz, CDCl3): d 8.41 (d, J 7.5 Hz, 1H), 8.13 (d, J 8.0 Hz, 1H),8.07 (d, J 8.0 Hz, 1H), 7.84 (t, J 7.5 Hz, 1H), 7.60 (t, J 7.0 Hz, 1H),7.49 (t, J 8.0 Hz, 1H), 7.39e7.34 (m, 2H); 13C NMR (125 MHz,CDCl3): d 161.2,151.3,134.82,134.77,130.6,130.4,128.9,124.5,122.8,121.7, 121.3, 118.1, 117.8.

According to the analysis of related databases, 2005-10-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Zhang, Jian; Shi, Dongdong; Zhang, Haifeng; Xu, Zheng; Bao, Hanyang; Jin, Hongwei; Liu, Yunkui; Tetrahedron; vol. 73; 2; (2017); p. 154 – 163;,
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Adding a certain compound to certain chemical reactions, such as: 51122-91-9, name is Dimethyl Isopropylmalonate, 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 51122-91-9, Application In Synthesis of Dimethyl Isopropylmalonate

Potassium hydroxide (32.2 g) and toluene (250 mL) were taken into a round bottom flask and stirred for about 10 minutes. Dimethylisopropyl malonate (50 g) and tetrabutylammonium bromide (10 g) were then added to it and again stirred for about 10 minutes, trans-lambda ,3-Dichloropropene (35 g) was added to the reaction mixture and maintained at about 30-35 C for about 4 hours. After the reaction was completed, the reaction mass was quenched with water (500 ml_) and stirred for about 10 minutes. The reaction mixture was extracted into toluene (250 ml_), and the toluene layer was washed with water and then evaporated under reduced pressure to afford 51 g (82% yield) of (£)-dimethyl 2- (3-chloroallyl)-2-isopropylmalonate as a dark brown viscous liquid. Purity by GC: 96.84%

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; DR. REDDY’S LABORATORIES LTD.; DR. REDDY’S LABORATORIES, INC.; KOLLA, Naveen Kumar; APPAYE, Kaliyaperumal Srinivasan; GANGULA, Srinivas; GOVINDAPUR, Rajeshwar Reddy; MANNE, Nagaraju; NIKUMBH, Satish Pandurang; NEELAM, Uday Kumar; JOSEPH, Suju Chuttippari; BADDAM, Sudhakar Reddy; KUNHIMON, Shyam Kumar Unniaranpurakkal; MOOVENDAN, Mohan; DAHANUKAR, Vilas; DONIPARTHI, Kiran Kumar; WO2012/21446; (2012); A2;,
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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. 6290-49-9, name is Methyl 2-methoxyacetate, A new synthetic method of this compound is introduced below., Product Details of 6290-49-9

Add 67.5g (1.25mol) to a 1000ml four-necked flaskSodium methoxide solid and 450ml of cyclohexane were heated to 50 C, and 52.0g (0.50mol) of methyl methoxyacetate was slowly added dropwise.Keep no more than 70 , about 1h dripping.Then keep the reaction at 80-90 for 16h. During this period, about 20ml of solvent was distilled off with water pump under reduced pressure every 3h, and 20ml of cyclohexane was added.The temperature was lowered to about 5 C, 6N hydrochloric acid was added to adjust pH = 6-7 (about 270ml), and then 200ml of water layer was added.The aqueous layer was extracted with cyclohexane (150 ml × 1), the organic layers were combined, washed with water (100 ml × 1), and decompressed under reduced pressure to obtain a brown liquid.Distillation under reduced pressure, collecting 114-115 C fraction (10 torr) to obtain intermediate III as a colorless transparent liquid, with a mass of 64.7 g, a yield of 73.7%, and a purity of 99.1%.

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; Nanjing Jieyun Pharmaceutical Technology Co., Ltd.; Zhou He; Shu Kai; Fang Jing; Zhang Li; Song Xingchang; Yu Zenghui; Wu Xiaodong; Liu Haomin; (10 pag.)CN111004121; (2020); A;,
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