Some scientific research about Methyl indole-4-carboxylate

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Related Products of 39830-66-5, The reaction rate of a catalyzed reaction is faster than the reaction rate of the uncatalyzed reaction at the same temperature.39830-66-5, Name is Methyl indole-4-carboxylate, molecular formula is C10H9NO2. In a Article£¬once mentioned of 39830-66-5

Rapid Syntheses of Heteroaryl-Substituted Imidazo[1,5-a]indole and Pyrrolo[1,2-c]imidazole via Aerobic C2-H Functionalizations

Here we report an aerobic Pd(0) catalyzed C2-H functionalization of indoles and pyrroles with tethered N-methoxylamide as the directing group. A Pd(0)-initiated mechanism overcomes the directing or poisoning effect from a wide range of heterocycles including pyridine, pyrimidine, and thiazole. The imidazo[1,5-a]indole products are transformed to bioactive analogs after one-step manipulations, demonstrating the potential utility of this reaction in drug discovery.

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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

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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.39830-66-5,Methyl indole-4-carboxylate,as a common compound, the synthetic route is as follows.

A 2M solution of oxalyl dichloride in DCM (1.712 mL, 3.425 mmol) was added to DCM (15 mL) in an ice-water bath. /V,/V-dimethylformamide (0.250 g, 3.425 mmol) was added dropwise under nitrogen. The reaction was stirred for 30 minutes at 0 C. Then methyl lH-indole-4-carboxylate (0.5 g, 2.854 mmol) in DCM (10 mL) was added. The reaction was warmed to room temperature and stirred for 1 hour. The solvent was removed. THF (15 mL) and 20% aqueous ammonium acetate were added. The reaction was stirred for 30 minutes under reflux (-70 C). The mixture was then extracted with ethyl acetate. The combined organic fractions were concentrated. The residue was purified by silica gel column chromatography to give the title compound (551 mg) as a white solid. LCMS m/z = 204.2 [M+H]+; NMR (400 MHz, CDC13) delta 4.00 (s, 3H), 7.34 (t, 7 = 7.8 Hz, 1H), 7.63 (dd, 7 = 8.0 and 1.0 Hz, 1H), 7.87 (dd, 7 = 7.5 and 1.0 Hz, 1H), 8.10 (d, 7 = 3.2 Hz, 1H), 9.08 (bs, 1H), 10.53 (s, 1H)., 39830-66-5

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Reference£º
Patent; ARENA PHARMACEUTICALS, INC.; SEMPLE, Graeme; BEHAN, Dominic P.; FEICHTINGER, Konrad; GLICKLICH, Alan; GROTTICK, Andrew J.; KAM, Maria Matilde Sanchez; KASEM, Michelle; LEHMANN, Juerg; REN, Albert S.; SCHRADER, Thomas O.; SHANAHAN, William R.; WONG, Amy Siu-Ting; ZHU, Xiuwen; WO2015/66344; (2015); 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