Category: 3196-15-4

Adding some certain compound to certain chemical reactions, such as: 3196-15-4, name is Methyl 2-bromobutyrate, 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 3196-15-4. 3196-15-4

[1014] Step 3: methyl 3-(1-methoxy-1-oxobutan-2-yl)-2-(4-methylbenzoylimino)-2,3-dihydrobenzo[d]thiazol-6-carboxylate[1015] To the mixture of methyl 2-(4-methylbenzamido)benzo[d]thiazol-6-carboxylate and 2-(4-methylbenzamido)benzo[d]thiazol-6-carboxylic acid (100 mg, 0.32 mmol) prepared in Step 2 in dimethylformamide (1.5 mL) were added potassium carbonate (133 mg, 0.96 mmol) and methyl 2-bromobutyrate (55 uL, 0.48 mmol). The reaction mixture was refluxed under stirring at 80 ? overnight. The reaction mixture was quenched with water and then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered, and then evaporated. The residue was purified with preparative thin layer chromatography (n-hexane/ethyl acetate = 4/1) to give 50 mg of the titled compound as a white solid (Yield: 37%).[1016] 1H NMR (DMSO-d 6 , 400 MHz) delta 8.61(s, 1H), 8.12(d, 1H), 8.06(d, 2H), 7.93(d, 1H), 7.34(d, 2H), 5.90(m, 1H), 3.90(s, 3H), 3.59(s, 3H), 2.40-2.50(m, 5H), 0.77(t, 3H)

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 Methyl 2-bromobutyrate.

Reference:
Patent; YUHAN CORPORATION; HUR, Youn; KIM, Dong-Hyun; KIM, Eun-Kyung; PARK, Jin-Hwi; JOO, Jae-Eun; KANG, Ho-Woong; OH, Se-Woong; KIM, Dong-Kyun; AHN, Kyoung-Kyu; WO2013/43001; (2013); A1;,
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3196-15-4, Name is Methyl 2-bromobutyrate, 3196-15-4, 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.

Example 1. Synthesis of benzo bis-furan compound IV-1 (1) In a round-bottom flask equiped with a reflux condenser and a magnetic stirrer, 0.5135g (1.0mmol) of compound I dissolved in 10mL DMF and 0.346g (2.5mmol) potassium carbonate was added. The reaction was stirred at room temperature. After ten minutes, 0.272g (1.5mmol) 2-bromobutyric acid methyl ester VI-a-1 was added and stirring was continued for 5h. After completion of the reaction, 30mL of dichloromethane was added with copious amount of water (80mL¡Á5) until removal of DMF. The organic phase was seperated, dried over anhydrous magnesium sulfate, concentrated, and purified by TLC (E/P [ethyl acetate:petroleum ether] = 1:5) to give the benzofuran II-a-1. Yield 75%

Statistics shows that Methyl 2-bromobutyrate is playing an increasingly important role. we look forward to future research findings about 3196-15-4.

Reference:
Patent; Zhejiang University; Wang, Yuguang; Zhu, Bingchun; Liu, Juanfang; Li, Qingsi; (14 pag.)CN104016998; (2016); B;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

3196-15-4, 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 3196-15-4 as follows.

Potassium carbonate (8.7 g, 63 mmol) was added to a solutionof 3-bromo-8-methylquinolin-6-ol (7, 5.0 g, 21 mmol) in 70 ml ofN,N-dimethylformamide. After the addition of methyl 2-bromobutyrate(7.1 g, 38 mmol), the reaction mixture was stirred for 16 h atroom temperature. Subsequently the mixture was filtered and thefiltrate was diluted with ethyl acetate. This organic phase waswashed with water and brine, dried over magnesium sulfate andevaporated under reduced pressure. The residue was purified bychromatography on silica gel, using ethyl acetate and cyclohexaneas eluents to yield 2-(3-bromo-8-methylquinolin-6-yloxy)-butyricacid methyl ester (8, 6.5 g, 19 mmol, 91%). 1H NMR (CDCl3):d = 1.04 (t, 3H, J = 7.3 Hz), 1.99 (q, 2H, J = 7.1 Hz), 2.68 (s, 3H),3.70 (s, 3H), 4.63 (t, 1H, J = 7.7 Hz), 6.65 (d, 1H, J = 2.3 Hz), 7.22(d, 1H, J = 2.2 Hz), 8.06 (d, 1H, J = 2.1 Hz), 8.68 (d, 1H, J = 2.1 Hz).LC-MS: Rt = 1.12 min; MS: m/z = 340 [M+1]+, 341 [M+2]+.

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

Reference:
Article; Lamberth, Clemens; Kessabi, Fiona Murphy; Beaudegnies, Renaud; Quaranta, Laura; Trah, Stephan; Berthon, Guillaume; Cederbaum, Fredrik; Knauf-Beiter, Gertrud; Grasso, Valeria; Bieri, Stephane; Corran, Andy; Thacker, Urvashi; Bioorganic and Medicinal Chemistry; vol. 22; 15; (2014); p. 3922 – 3930;,
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 3196-15-4 as follows. 3196-15-4

Step 4: methyl 2-(6-(azetidin-1-carbonyl)-2-((4-methylbenzoyl)imino)benzo[d]thiazol-3(2H)-yl)butanoate To a solution of N-(6-(azetidin-1-carbonyl)benzo[d]thiazol-2(3H)-ylidene)-4-methylbenzamide (91 mg, 0.26 mmol), prepared in Step 3, in N,N-dimethylformamide (1.0 mL) were added potassium carbonate (108 mg, 0.78 mmol) and methyl 2-bromobutyrate (45 uL, 0.39 mmol). The reaction mixture was stirred at 80 C. overnight and then cooled to room temperature. The reaction mixture was and quenched with water and then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered, and then evaporated. Diisopropyl ether and ethyl acetate were added to the filtrate. The resulting mixture was stirred for 5 minutes and then filtered. The resulting solid was washed with diisopropyl ether, and then dried under reduced pressure to give 61 mg of the titled compound as a white solid (Yield: 52%). 1H NMR (CDCl3, 400 MHz) delta 8.18 (d, 2H), 8.01 (s, 1H), 7.73-7.88 (m, 2H), 7.26-7.31 (m, 2H), 5.54-5.62 (m, 1H), 4.27-4.38 (m, 3H), 3.66 (s, 3H), 3.13 (m, 1H), 2.37-2.54 (m, 7H), 0.90 (t, 3H)

According to the analysis of related databases, 3196-15-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; YUHAN CORPORATION; Hur, Youn; Kim, Dong-Hyun; Kim, Eun-Kyung; Park, Jin-Hwi; Joo, Jae-Eun; Kang, Ho-Woong; Oh, Se-Woong; Kim, Dong-Kyun; Ahn, Kyoung-Kyu; US2015/11528; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

3196-15-4, name is Methyl 2-bromobutyrate, 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. 3196-15-4

1.80 g (9.66 mmol) of tert-butyl 2-(aminomethyl)azetidine-1-carboxylate [racemate] were dissolved in 25 ml of dichloromethane, 1.62 ml (1.17 g, 11.6 mmol) of triethylamine and 1.11 ml (1.75 g, 9.66 mmol) of methyl 2-bromobutanoate [racemate] were added and the mixture was stirred under reflux overnight. 1.35 ml (0.98 g, 9.66 mmol) of triethylamine and 0.89 ml (1.40 g, 7.73 mmol) of methyl 2-bromobutanoate [racemate] were then added, and the mixture was stirred under reflux overnight. After cooling to room temperature, water was added and the phases were separated. The aqueous phase was extracted twice with dichloromethane and the combined organic phases were washed with saturated aqueous sodium chloride solution, dried over sodium sulphate, filtered and then freed of the solvent under reduced pressure. This gave 2.64 g (83% of theory, purity: 87%) of the desired product. LC-MS (Method 6A): Rt=2.16 min (diastereomer 1, 2 isomers), Rt=2.22 min (diastereomer 2, 2 isomers); MS (ESIpos): m/z=287 [M+H]+

Statistics shows that 3196-15-4 is playing an increasingly important role. we look forward to future research findings about Methyl 2-bromobutyrate.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; ALLERHEILlGEN, Swen; BUCHMUeLLER, Anja; ENGEL, Karen; GERDES, Christoph; GERICKE, Kersten Matthias; GERISCH, Michael; HEITMEIER, Stefan; HILLlSCH, Alexander; KINZEL, Tom; LIENAU, Philip; RIEDL, Bernd; ROeHRIG, Susanne; SCHMIDT, Martina Victoria; STRASSBURGER, Julia; TERSTEEGEN, Adrian; (135 pag.)US2016/108027; (2016); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

3196-15-4, These common heterocyclic compound, 3196-15-4, name is Methyl 2-bromobutyrate, 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.

Example 1Preparation of methyl 2-(6-methoxy-lH-inden-3-yl) butanoateAn oven dried 5 -L four-necked round -bottomed flask was fitted with a thermometer, a condenser, an addition funnel, and a mechanical stirrer. Under Ar protection, a suspension of 5-methoxy-l-indanone (80.0 g, 494 mmol), Zn powder (Lancaster, 56.2 g, 865 mmol) in 2 L anhydrous TEtaF was stirred at 6O0C (internal temperature), while a solution of methyl bromobutyrate (134.1 g, 74] mmoi) in 400 inL anhydrous TEtaF was added slowly through an addition funnel After completion of the addition, the reaction mixture was stirred at 6O0C (internal temperature) for 1 hour. The reaction was followed by TLC analysis of aliquots following IN aqueous HCl work-up. After the reaction was completed, it was cooled in an ice-water bath followed by slow addition of 3 L of IN HCl solution. The pot temperature was kept below 2O0C. The mixture was then extracted with 1 L EtOAc. The organic layer was washed with water until pH 6.0-7.0, then saturated NaCl solution, and dried over Na2SO4, The product (127 g, >;99%), a yellow oil, was obtained after solvent removal and drying under vacuum. 1H NMR (DMSO-t,) delta 7.28(d, IH), 7.05(d, IH), 6.82(dd, IH), 6.22(s, IH), 3.72(s, 3H), 3.60(m, IH), 3.58(s, 3H), 3.28(s, 2H), 1.95(m, IH), 1.80(m, IH), 0.88(t, 3H).

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 3196-15-4.

Reference:
Patent; DARA BIOSCIENCES, INC.; DELMEDICO, Mary Katherine; WO2010/141696; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics