Category: esters-buliding-blocks

Application of 1186-73-8, 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 1186-73-8 as follows.

Step 13; methyl 10-(((tert-butyldimethylsilyl)oxy)methyl)-l-(2,4-dimethoxybenzyl)-4- hydroxy-9-methyl-2-oxo-2,5,6,9-tetrahydro-lH-pyrido[2′,3′:4,5]oxepino[3,2- f] indole-3-carboxylate A solution of N-(8-((tert-butyldimethylsilyloxy)methyl)-9-methyl-3,4-dihydro-2H- oxepino[3,2-f]indol-5(9H)-ylidene)-l-(2,4-dimethoxyphenyl)methanamine (3.81 g crude) and trimethyl methanetricarboxylate (2.9 g, 15.0 mmol) in Ph20 (15 mL) was heated at 230 C for 15 min. The reaction mixture was cooled to room temperature and purified on silica gel using EtO Ac/Hex (0-60% gradient) to afford the product (2.0 g, 43%) as a yellow foam. XH NMR (500 MHz, DMSO-i) delta ppm 0.00 (d, J=0.95 Hz, 6 H) 0.77 – 0.83 (m, 9 H) 1.87 – 1.96 (m, 2 H) 2.88 – 2.96 (m, 1 H) 3.48 (s, 3 H) 3.64 (d, J=1.89 Hz, 6 H) 3.77 (s, 3 H) 4.21 (br. s., 2 H) 4.74 (s, 2 H) 4.98 – 5.07 (m, 1 H) 6.24 (s, 1 H) 6.37 (s, 2 H) 6.61 – 6.68 (m, 1 H) 7.21 (s, 1 H) 7.31 – 7.40 (m, 1 H) 13.28 – 13.36 (m, 1 H). LC-MS: 633.2 [M-H]”, RT 1.80 min.

According to the analysis of related databases, 1186-73-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PTC THERAPEUTICS, INC.; BRANSTROM, Arthur; JOSYULA, Vara Prasad, Venkata Nagendra; ARNOLD, Michael, Andrew; GERASYUTO, Aleksey, I.; KARP, Gary; WANG, Jiashi; WO2013/33228; (2013); A1;,
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These common heterocyclic compound, 619-42-1, name is Methyl 4-bromobenzoate, 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. Computed Properties of C8H7BrO2

To a stirred solution of methyl 4-bromobenzoic acid methyl ester (45 g, 209.0 mmol) in MeOH (500 mL), hydrazine hydrate (39.31 g, 627.0 mmol) was added at RT and heated to 65 C for 12h. After cooling the reaction mixture to RT, the solvent was removed under reduced pressure. The residue was slurred with diethyl ether (300 mL). The solid was filtered off and dried under suction to afford the title compound as an off white solid (40 g, 93% yield). NMR (400 MHz, DMSO-d6) delta 9.84 (s, 1H), 7.76- 7.73 (m, 2H), 7.66-7.64 (m, 2H), 4.49 (s, 2H) 1H NMR (DMSO-d6, 400MHz) delta 9.84 (s, 1H), 7.76-7.73 (m, 2H), 7.66-7.63 (m, 2H), 4.42 (b, 2H). LC/MS (Method A): 217.0(M+H)+. HPLC (Method F) Rt 2.02 min (Purity: 99.6%).

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

Reference:
Patent; ARES TRADING S.A.; QUATTROPANI, Anna; SWINNEN, Dominique; WO2013/182274; (2013); 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. 55666-43-8, name is tert-Butyl 3-bromopropanoate, A new synthetic method of this compound is introduced below., HPLC of Formula: C7H13BrO2

To a stirred mixture of 3-[(methylamino)methyl]benzonitrile (6.1 g, 41.7 mmol) and sodium bicarbonate (7.0 g, 83.4 mmol) in ACN (70 mL) was added dropwise tert-butyl 3-bromo- propanoate (7 mL, 41.7 mol). After being stirred at RT for 12 hours, the reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by chromatography (silica, pet ether/EtOAc) to afford the title compound as a pale yellow liquid. 1H NMR (DMSOd6, 400 MHz) delta 7.70 (s, 2H), 7.60 (m, 1 H), 7.51 (m, 1 H), 3.49 (s, 2H), 2.58 (m, 2H), 2.36 (m, 2H), 2.09 (s, 3H), 1.38 (s, 9H).

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; MERCK SERONO S.A.; QUATTROPANI, Anna; MONTAGNE, Cyril; SAUER, Wolfgang; CROSIGNANI, Stefano; BOMBRUN, Agnes; WO2010/112461; (2010); A1;,
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Application of 18595-18-1, 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. 18595-18-1, name is Methyl 3-amino-4-methylbenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Compound (1b) 10.00 g (0.06 mol), cyanamide 5.08 g (0.12 mol),50 mL of ethanol was charged and the temperature was raised to 70 C. After dropping 7.12 g (0.07 mol) of concentrated sulfuric acid over 6 hours, the mixture was stirred under reflux for 2 hours.After the completion of the reaction, the reaction mass was cooled to 5 C., kept warm, filtered,Washed with 40 mL of ethanol. The obtained crystals were dried under reduced pressure,14.53 g (yield 93.7%) of 1/2 sulfate of the compound (2b) was obtained.LC area percentage 100%

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 3-amino-4-methylbenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sumitomo Chemical Co., Ltd.; Kumazawa, Hiroharu; Nishimori, Nobuaki; Okura, Yuka; (15 pag.)JP2020/2108; (2020); A;,
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Some common heterocyclic compound, 431-47-0, name is Methyl 2,2,2-trifluoroacetate, molecular formula is C3H3F3O2, 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. Recommanded Product: 431-47-0

General procedure: Amixture of carbazole 5-h (0.68 mmol) and THF (15 ml)was stirred and treated by the addition of LiH (0.03 g,3.40 mmol) and methyl trifluoroacetate (0.26 g,2.03 mmol). The reaction mixture was stirred for 1.5-5 h at63, evaporated, and treated with cold 5% hydrochloricacid solution (20 ml). The precipitate was filtered off,washed with water, and then dried over P2O5.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 431-47-0, its application will become more common.

Reference:
Article; Pugachov, Dmitriy E.; Kostryukova, Tatiana S.; Zatonsky, Georgy V.; Vatsadze, Sergey Z.; Vasil?ev, Nikolai V.; Chemistry of Heterocyclic Compounds; vol. 54; 5; (2018); p. 528 – 534; Khim. Geterotsikl. Soedin.; vol. 54; 5; (2018); p. 528 – 534,7;,
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Application of 15012-36-9, A common heterocyclic compound, 15012-36-9, name is Methyl 2,3-dimethylbenzoate, molecular formula is C10H12O2, 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.

Methyl 2,3-dimethylbenzoate was dissolved in concentrated sulfonic acid (10 mL). KNO3 (808 mg, 1.2 eq.) was added to the solution at 0 C., then slowly warmed to rt overnight. The reaction was quenched with water (80 mL), extracted with ethyl acetate (2¡Á80 mL). The organic layers were evaporated to give mixture of nitrated ester and acid (1:1). The mixture was redissolved in DMF (10 mL). K2CO3 (1.1 g) and iodomethane (0.5 mL) were added to the solution. The reaction was stirred at rt for three days, then diluted with water (80 mL). It was extracted with ethyl acetate (3¡Á80 mL) and evaporated. The residue was purified by column chromatography (EtOAc in hexanes=0-30% in 45 min) to give the desired nitrobenzoate ester. 1H NMR (300 MHz, DMSO) delta 8.31 (s, 1H), 8.24 (s, 1H), 3.86 (s, 3H), 2.46 (s, 3H), 2.40 (s, 3H).

The synthetic route of 15012-36-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Rigel Pharmaceuticals, Inc.; US2012/28923; (2012); A1;,
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Synthetic Route of 23426-63-3, A common heterocyclic compound, 23426-63-3, name is Methyl 2-bromo-2-methylpropanoate, 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.

General procedure: Toa solution of 1a (770 mg, 3.24 mmol) in DMF (20 mL) was added potassium carbonate (2.69g, 19.5 mmol).Thereaction mixture was stirred at ambient temperature for 30minutes. After addition of ethyl bromoacetate (1.08mL), the mixture was heated at 70oC for 2 hours. The mixture was cooled to ambient temperature andwater (60 mL) was added. The solution was extractedwith ethyl acetate (3 30 mL). The organic phase was washed withsaturated aqueous sodium chloride solution (2 ¡Á 15mL), dried over sodium sulfate, filtered and concentrated. The residue waspurified by column chromatography (silica gel, petroleum ether/ethyl acetate 5:1)to give the title compound (464 mg, 44% yield) as 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:
Article; Huang, Yaping; Sun, Geng; Wang, Pengfei; Shi, Rui; Zhang, Yanchun; Wen, Xiaoan; Sun, Hongbin; Chen, Caiping; Bioorganic and Medicinal Chemistry Letters; vol. 28; 17; (2018); p. 2957 – 2960;,
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Synthetic Route of 2396-84-1, These common heterocyclic compound, 2396-84-1, name is Ethyl sorbate, 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 diisopropyl amine (3.5 mL, 25.0 mmol) in dry THF (12 mL) cooled at -10 ¡ãC under a nitrogen atmosphere was added a solution of n-BuLi (10 mL, 2.5 M in hexanes, 25.0 mmol) followed by stirring for 30 min at the same temperature. The resultant LDA solution was then cooled to -78 ¡ãC, and, after adding HMPA (4 mL), was stirred for another 20 min at -78 ¡ãC.To the above prepared LDA-HMPA solution was added a solution of ethyl sorbate (8, 1.50 mL, 10.0 mmol) in dry THF (5 mL). After stirring at -78 ¡ãC for 1.5 h, the reaction was quenched by adding a mixed solution of water (22 mL) and acetic acid (4 mL). The reaction mixture was extracted with hexane (30 mL.x.3) and the combined organic layer was washed with saturated aqueous NaHCO3 and brine, dried over anhydrous Na2SO4, filtered off, and concentrated under reduced pressure to give the crude deconjugate ester, which was used for next reaction without purification.

The synthetic route of 2396-84-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wu, Jinlong; Jiang, Xiuqing; Xu, Jingjing; Dai, Wei-Min; Tetrahedron; vol. 67; 1; (2011); p. 179 – 192;,
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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. 37466-90-3, name is Ethyl 3,4-diaminobenzoate, A new synthetic method of this compound is introduced below., SDS of cas: 37466-90-3

General procedure: A flask was charged with o-phenylenediamine (1a; 54 mg, 0.5 mmol), hexafluoroacetylacetone (2; 125 mg, 0.6 mmol), Fe(OTf)3 (25 mg, 0.05 mmol), DMF (2.0 mL). The reaction was stirred at 80 C for 24 h, when the reaction was complete monitored by TLC, the mixture was cooled to room temperature. Water (10 mL) was added to the mixure, and then extracted with EtOAc (3¡Á30 mL). The combined organic phase was washed with water, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the product 3a (92 mg, 99%) as yellow 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:
Article; Zhou, Yanmei; Shen, Guanshuo; Sui, Yuebo; Zhou, Haifeng; Tetrahedron Letters; vol. 57; 30; (2016); p. 3396 – 3399;,
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46193-76-4, name is Ethyl 4H-thieno[3,2-b]pyrrole-5-carboxylate, 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. Product Details of 46193-76-4

To a solution of 4H-thiophene [3,2-b] pyrrole-5-carboxylic acid ethyl ester (4.24 g, 21.7 mmol) in DMF (20 mL) at room temperature was added K2CO3 (7.82 g, 56.6 mmol),Then iodomethane (2.52 g, 17.8 mmol) was added dropwise.The mixture was stirred at room temperature for 2 h.The reaction was quenched with water and extracted with EtOAc (3 ¡Á).The combined organic phases were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure.The residue was purified by silica gel chromatography,Elution with 0-10% EtOAc in hexanes gave the title compound (3.96 g, 18.9 mmol, 87% yield).

The synthetic route of 46193-76-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Beijing Jiakesitu Drug Discovery Co., Ltd.; Beijing Jiakesi Drug Discovery Co., Ltd.; Fang Haiquan; Li Haijun; Yang Guiqun; Wang Yanping; Wu Lingjun; Li Qinglong; Du Yuelei; Zhang Lei; Hu Shaojing; (65 pag.)CN110407854; (2019); A;,
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