Category: 61019-05-4

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.61019-05-4,5-Methoxy-7-methyl-1H-indole,as a common compound, the synthetic route is as follows.

61019-05-4, Oxalyl chloride (0.17 mL, 1.93 mmol) was added dropwise via syringe over 1 min to DMF (1.5 mL) in a vial charged with a magnetic stir bar under N2 at 0 C. After ~30 min, 5-methoxy-7-methyl-1H-indole (342 mg, 2.123 mmol) was added dropwise via syringe over ~30 s as a solution in DMF (2 mL). The reaction was allowed to warm to room temperature and stir overnight, after which 1 N NaOH (2 mL) was added dropwise via syringe over 30 s. The reaction was then heated to 100 oC for 20 min, after which it was cooled to room temperature. After 28 h of total reaction time, the mixture was diluted with H2O (15 mL) and DCM (20 mL). The organic layer was separated, and the aqueous layer was washed with DCM (10 mL). The combined organic layers were washed with H2O (2 × 15 mL) and brine (10 mL), dried with Na2SO4, filtered, and concentrated in vacuo to provide a dark red crude residue. The crude material was purified via flash chromatography on silica (24 g column, 0-60% EtOAc/heptane) to afford 300 mg (82% yield) of 13 as a pale yellow solid. 1H NMR (400 MHz, DMSO-d6) delta ppm 12.27 – 11.84 (m, 1H), 9.89 (s, 1H), 8.20 (d, J = 3.30 Hz, 1H), 7.41 (d, J = 2.45 Hz, 1 H), 6.71 (dd, J = 2.32, 0.73 Hz, 1H), 3.76 (s, 3H), 2.48 – 2.43 (m, 3H); LCMS m/z = 190.2 ([M+H]+), tR = 1.00 min (method A).

The synthetic route of 61019-05-4 has been constantly updated, and we look forward to future research findings.

Reference：
Article; DeChristopher, Brian; Park, Soo-Hee; Vong, Linh; Bamford, Derek; Cho, Hyun-Hee; Duvadie, Rohit; Fedolak, Allison; Hogan, Christopher; Honda, Toshiyuki; Pandey, Pramod; Rozhitskaya, Olga; Su, Liansheng; Tomlinson, Elizabeth; Wallace, Iain; Bioorganic and Medicinal Chemistry Letters; vol. 29; 8; (2019); p. 991 – 994;,
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

61019-05-4,61019-05-4, 5-Methoxy-7-methyl-1H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of 5-methoxy-7-methyl-1H-indole (CAS: 61019-05-4, 9.69 g, 60.1 mmol) inCH2CI2 (200 mL) at room temperature was added Boc2O (19.54 ml, 84 mmol), DMAP (0.734 g, 6.01 mmol), and Et3N (10.05 ml, 72.1 mmol). The mixture was then stirred for 16h. The reaction wasdiluted with CH2CI2 and saturated NH4CI. The aqueous phase was extracted three times withCH2CI2. The organic phase was washed with brine, dried over Na2504, filtered, and concentrated.The resulting residue was purified by silica gel flash column chromatography (EtOAc/heptanes) toprovide the title compound. MS (ESl+) m/z 262.2 (M+H).

The synthetic route of 61019-05-4 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; NOVARTIS AG; ADAMS, Christopher; CAPPARELLI, Michael Paul; EHARA, Takeru; KARKI, Rajeshri Ganesh; MAINOLFI, Nello; ZHANG, Chun; WO2015/9616; (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

61019-05-4, 5-Methoxy-7-methyl-1H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

61019-05-4, To a 250 ml round bottom flask was added 7-methyl-5-methoxy-lH-indole (50 mmol)Add 100 ml of toluene to mix it,Further addition of cinnamoyl chloride (60 mmol)Room temperature reaction for 1 hour,After the compound has been completely precipitated,Phenylhydrazine (60 mmol) was added,Heated to 105 C with a heating jacket,Placed on a magnetic stirrer,The reaction was heated under reflux for 6 hours,Reaction process constantly point observation,After the reaction is complete, the heating is stopped and the condensing unit is removed.The reaction solution was distilled and concentrated, and the product was isolated by column chromatography.The crude product was recrystallized from an ethanol-water solution, dried,The product was obtained (pale pink solid 12.71 g, yield 80.2%).

As the paragraph descriping shows that 61019-05-4 is playing an increasingly important role.

Reference：
Patent; Shaanxi University of Science and Technology; Liang Chengyuan; Song Huihui; Zhang Shiyun; Mao Gennian; (17 pag.)CN104230786; (2017); B;,
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

61019-05-4,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.61019-05-4,5-Methoxy-7-methyl-1H-indole,as a common compound, the synthetic route is as follows.

General procedure: In a typical reaction, DAC (0.20 mmol) was mixed with indole (0.20 mmol) and PTSA (10 mol%) in ethanol (1.0 mL). The mixture was then stirred at 60C for 20 min. After reaction, the mixture was cooled to room temperature, and the product was obtained by isolation with preparative TLC (eluting solution: petroleum ether/ethyl acetate=5/1 (v/v)). Tests for substrate scope were all performed with an analogous procedure. Large scale synthesis was also performed in a similar procedure. The product was isolated by silica column chromatography (eluting solution: petroleum ether/ethyl acetate=8/1 (v/v)).

61019-05-4 5-Methoxy-7-methyl-1H-indole 12338917, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Article; Liu, Changhui; Zhou, Li; Huang, Wenbo; Wang, Man; Gu, Yanlong; Tetrahedron; vol. 72; 4; (2016); p. 563 – 570;,
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