Category: 125872-95-9

Chemistry is the experimental science by definition. We want to make observations to prove hypothesis. For this purpose, we perform experiments in the lab. 125872-95-9, Name is 6-Bromo-1-methyl-1H-indole,introducing its new discovery., 125872-95-9

Palladium-Catalyzed alpha-Arylation of Vinylogous Esters for the Synthesis of gamma,gamma-Disubstituted Cyclohexenones

A palladium-catalyzed alpha-arylation of cyclic vinylogous esters to form products that are converted in one step to gamma-alkyl-gamma-aryl-substituted cyclohexenones is reported. This Pd-catalyzed reaction proceeds at room temperature, is generally high-yielding, and uses an amount of a commercially available catalyst as low as 0.25 mol %. The scope of aryl bromides is particularly broad, and alkenyl bromides can also be used. This two-step protocol, comprising alpha-arylation and reductive transposition, can be performed in one pot and is applicable to gram-scale synthesis.

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Reference£º
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.125872-95-9,6-Bromo-1-methyl-1H-indole,as a common compound, the synthetic route is as follows.

Preparation of 2-(6-bromo-1-methyl-1H-indol-3-yl)ethanol To a solution of 6-bromo-1-methyl-1/1-indole (18.0 g, 85.6 mmol) in diethyl ether (180 mL) at 0 C., was added oxalyl chloride (13.1 g, 103 mmol) dropwise under a nitrogen atmosphere. The resulting mixture was allowed to warn to room temperature and stirred for 1 h. After this time, methanol (15 mL) was added and the reaction stirred at room temperature further for 24 h. After this time, the reaction was filtered and the filter cake washed with water (20 mL), then cold diethyl ether (20 mL). The filter cake was dissolved in methylene chloride (100 mL) and dried over sodium sulfate. The drying agent was removed by filtration and the filtrate concentrated under reduced pressure to afford methyl 2-(6-bromo-1-methyl-1H-indol-3-yl)-2-oxoacetate which was used in the next step without purification. A suspension of methyl 2-(6-bromo-1-methyl-1H-indol-3-yl)-2-oxoacetate (18.0 g, 60.8 mmol) in tetrahydrofuran (200 mL) was treated with 2 M borane dimethylsulfide complex in tetrahydrofuran (121 mL) and stirred at reflux for 5 h. After this time, the reaction was cooled to room temperature, diluted with water (50 mL) and saturated aqueous sodium bicarbonate (100 mL) and extracted with diethyl ether (3*250 mL). The combined organic layers were washed sequentially with water and brine, dried over sodium sulfate, filtered and the filtrate concentrated under reduced pressure to afford 2-(6-bromo-1-methyl-1H-indol-3-yl)ethanol as a white solid: 1H NMR (400 MHz, CDCl3) d 7.46 (d, J=8.4 Hz, 1H), 7.46 (d, J=1.6 Hz, 2H), 7.22 (dd, J=8.4, 1.6 Hz, 1H), 6.92 (s, 1H), 3.88 (t, J=6.4 Hz, 2H), 3.73 (s, 3H), 2.99 (t, J=6.4 Hz, 3H).

125872-95-9, 125872-95-9 6-Bromo-1-methyl-1H-indole 15546854, aindole-building-block compound, is more and more widely used in various fields.

Reference£º
Patent; Gilead Connecticut, Inc.; Blomgren, Peter A.; Currie, Kevin S.; Kropf, Jeffrey E.; Lee, Seung H.; Mitchell, Scott A.; Schmitt, Aaron C.; Xu, Jianjun; Zhao, Zhongdong; US2014/148430; (2014); A1;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

125872-95-9, 6-Bromo-1-methyl-1H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: Indole-6-boronic acid (274 mg, 1.7 mmol) and 7a (516 mg, 1.5 mmol)were added into a 100 mL round-bottom flask containing 1,4-dioxane (10 mL), then 25.2 mgPd(PPh3)2Cl2 was added, followed by 1.0 mL 2.0 M K2CO3. The mixture was stirred and heatedto reflux under Argon for about 4 hours. After the reaction was complete, the mixture was cooledto room temperature, 10.0 mL H2O was added and the product was extracted with ethyl acetate(10 mL¡Á3). The organic solvent was combined, dried (anhydrous Na2SO4), filtered andevaporated. The crude product was purified by chromatographic column using hexane : ethylacetate (4:1) as eluent. 380.1 mg methyl 3-[[6-(1H-indol-6-yl)indol-1-yl]methyl]benzoate wasobtained as pale yellow oil, yield 67%.

125872-95-9, The synthetic route of 125872-95-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Zhou, Guangyan; Chu, Shidong; Nemati, Ariana; Huang, Chunsheng; Snyder, Beth A.; Ptak, Roger G.; Gochin, Miriam; European Journal of Medicinal Chemistry; vol. 161; (2019); p. 533 – 542;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles