Category: 609-12-1

609-12-1, 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 609-12-1 as follows.

[00281] 3-Methyl-2-(2-methyl-1H-indol-4-yloxy)-butyric acid ethyl ester (2): A mixture of 4-hydroxy-2-methylindole (1) (1.5 g, 0.010 mole), 2-bromo-3-methyl-butyric acid ethyl ester (2.2 g, 0.010 mole) and potassium carbonate (excess) in acetone (50 mL) was refluxed for 3 days. The reaction mixture was filtered, and the filtrate was concentrated. The residue was purified by column chromatography (20:1 Hex:EtOAc) to afford intermediate 2. Yield: 1.88 g, 71 %

According to the analysis of related databases, Ethyl 2-bromo-3-methylbutanoate, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ILYPSA, INC.; WO2007/56280; (2007); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

609-12-1, name is Ethyl 2-bromo-3-methylbutanoate, 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. 609-12-1

Into a 100-mL round-bottom flask, was placed 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1.9 g, 10.0 mmol, 1.00 equiv), N,N-dimethylformamide (30 mL), ethyl 2-bromo-3-methylbutanoate (2.1 g, 10.0 mmol, 1.0 equiv), and cesium carbonate (10.0 g, 30.7 mmol, 3.0 equiv). The resulting solution was stirred for 12 hours at 90 C. The reaction was then quenched by the addition of 10 mL of water. The resulting solution was extracted with ethyl acetate (20 mL*3), and the organic layers combined and concentrated under vacuum. The residue was applied onto a silica gel column eluting with ethyl acetate/petroleum ether (1:6). This resulted in 3.3 g (93%) of ethyl 3-methyl-2-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]butanoate as a white solid.

Statistics shows that 609-12-1 is playing an increasingly important role. we look forward to future research findings about Ethyl 2-bromo-3-methylbutanoate.

Reference:
Patent; Arvinas Operations, Inc.; Genentech, Inc.; Crew, Andrew P.; Wang, Jing; Berlin, Michael; Dragovich, Peter; Chen, Huifen; Staben, Leanna; US2019/300521; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 609-12-1, name is Ethyl 2-bromo-3-methylbutanoate, molecular formula is C7H13BrO2, 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. 609-12-1

General procedure: To a solution of sodium methoxide (prepared from 0.1mol of sodium in anhydrous MeOH (60mL)), 0.05mol of 1 and 0.055mol of ester (2a-h) were added and refluxed 1-3h (chromatographic control TLC). The solvent was evaporated and the residue was dissolved in water and neutralized with HCl to pH=7-8. The product was extracted with CHCl3, dried, concentrated, and crystallized from diethyl ether.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 609-12-1, its application will become more common.

Reference:
Article; Studzi?ska, Renata; Ko?odziejska, Renata; Kupczyk, Daria; P?azi?ski, Wojciech; Kosmalski, Tomasz; Bioorganic Chemistry; vol. 79; (2018); p. 115 – 121;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 609-12-1, name is Ethyl 2-bromo-3-methylbutanoate, 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. 609-12-1

A) ethyl 2-(3-cyano-4-methoxy-2-oxopyridin-1(2H)-yl)-3-methylbutanoate (0774) A mixture of 4-methoxy-2-oxo-1,2-dihydropyridine-3-carbonitrile (5.0 g), ethyl 2-bromo-3-methylbutanoate (10.4 g), cesium carbonate (32.6 g) and N,N-dimethylformamide (75 mL) was stirred at 50C overnight. The reaction mixture was added to water, and the mixture was extracted twice with ethyl acetate. The extracts were combined, washed with water and then saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (6.11 g). MS (ESI+): [M+H]+ 279.2.

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 609-12-1.

Reference:
Patent; Takeda Pharmaceutical Company Limited; YOSHIDA, Masato; NAGAMIYA, Hiroyuki; OHBA, Yusuke; SETO, Masaki; YOGO, Takatoshi; SASAKI, Satoshi; TOKUNAGA, Norihito; ASO, Kazuyoshi; (298 pag.)EP2980089; (2016); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics