Category: 525593-33-3

525593-33-3,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.525593-33-3,3-Bromo-5-nitroindole,as a common compound, the synthetic route is as follows.

General procedure: A mixture of 5-nitro-1H-indole (200mg, 1.23mmol) or its derivatives and dry DMF (5mL) was cooled to 0C and NaH (60mg, 1.23mmol) was added. After the addition, the reaction mixture was stirred at r.t. for 0.5-1h, then compound 4 (282mg, 1.23mmol) was added, and the reaction mixture was allowed to stirred for an additional 2h. After a sequence of extraction, wash, and concentration, the crude product compound 5 (222mg, 0.72mmol, 58.30%) was obtained and could be used in next step without further purifications [12].

As the paragraph descriping shows that 525593-33-3 is playing an increasingly important role.

Reference：
Article; Wu, Zeng; Yan, Ming; Hu, Shi-He; Yu, Zhi-Cheng; Zhu, Yong; Cheng, Ya-Dong; Liu, Hai-Chun; Zhang, Yan-Min; Yao, Si-Hui; Tang, Wei-Fang; Lu, Tao; Chinese Chemical Letters; vol. 25; 2; (2014); p. 351 – 354;,
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

525593-33-3, 3-Bromo-5-nitroindole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of the 3-bromo-5-nitro-1H-indole (200 mg, 0.83 mmol) and tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-1-carboxylate (267 mg, 0.91 mmol) in THF (10 mL) was added Na2CO3 (175 mg, 1.7 mmol) in H2O (3 mL). The mixture was degassed and refilled with nitrogen for 3 times. Then Pd (PPh3)2Cl2 (47 mg, 0.065 mmol) was added to the above mixture and the mixture was degassed for another 3 times. The mixture was heated to reflux for overnight. Then the reaction mixture was concentrated in vacuo and the residue was extracted with ethyl acetate. The combined organic layer was dried (Na2SO4), and concentrated to get crude product, which was purified by column chromatography on 100-200 mesh silica gel to afford the title compound (100 mg, 37%) as yellow solid. 1H NMR (400 MHz, CDCl3): delta ?81 (d, J=1.2 Hz, 1H), 8.50 (br.s, 1H), 8.14-8.17 (dd, J=2.0, 8.8 Hz, 1H), 7.56 (s, 1H), 7.36-7.46 (m, 3H), 6.53-6.52 (m, 1H), 1.65 (s, 9H). LCMS: m/e 327.85 [M+H]+, 525593-33-3

The synthetic route of 525593-33-3 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; PFIZER INC.; Schnute, Mark Edward; Wennerstal, Goeran Mattias; Blinn, James Robert; Kaila, Neelu; Kiefer, JR., James Richard; Mente, Scot Richard; Kurumbail, Ravi G.; Meyers, Marvin Jay; Thorarensen, Atli; Xing, Li; Zapf, Christoph Wolfgang; Zamaratski, Edouard; Flick, Andrew Christopher; Jones, Peter; (77 pag.)US2016/46597; (2016); 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

525593-33-3,525593-33-3, 3-Bromo-5-nitroindole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step B: A solution of 3-bromo-5-nitroindole from above (625 mg, 2.1 mmol), phenylboronic acid (381 mg, 3.13 mmol), triphenylphosphine (109.3 mg, 0.417 mmol) in dimethoxyethane (4.16 mL) was degassed. To this mixture 2N sodium carbonate (6.25 mL) was added, and reaction mixture was degassed again. To the reaction was added palladium (II) acetate (23.4mg, 0.104 mmol), and the reaction was refluxed under dry nitrogen with stirring for 8 hours. The reaction mixture was then diluted with 1 M HCl (100 mL), and extracted with ethyl acetate (100 mL). The organic phase was washed with water (100 mL), and brine (100 mL). The organic phase was dried over MgSO4 and concentrated in vacuo. The crude product was purified by chromatography over silica gel (EtOAc/hexanes, 10/90) to afford 3-phenyl-5-nitroindole as an orange powder (45 mg, 9% yield).

The synthetic route of 525593-33-3 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; PTC THERAPEUTICS, INC.; HWANG, Peter Seongwoo; TAKASUGI, James; REN, Hongyu; WILDE, Richard Gerald; TURPOFF, Anthony; AREFOLOV, Alexander; KARP, Gary Mitchell; CHEN, Guangming; CAMPBELL, Jeffrey Allen; WO2006/19831; (2006); 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

525593-33-3,525593-33-3, 3-Bromo-5-nitroindole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 1 : 3-Bromo-1-methyl-5-nitro-1 /-/-indole. To a solution 3-bromo-5-nitro-1 H-indole (5.5 g, 20.6 mmol) in THF (50ml_) at 0 C was added NaH (1.9 g, 41.3 mmol, 60% w/w in mineral oil). The mixture was stirred for 15 min and methyl iodide (6.4 ml_, 103.3 mmol) was added. The reaction mixture was warmed to room temperature and stirred for 16 h. After completion, the reaction mixture was cooled, quenched with addition of ice-cooled water and extracted using EtOAc. The combined organic layer was dried over anhydrous Na2S04i filtered and concentrated to obtain a crude product which was purified by triturating with diethyl ether to afford the title compound (5 g, 86%). 1H NMR (400 MHz, CDCI3) delta 8.55 (d, J = 2.4 Hz, 1 H), 8.17 (dd, J = 8.8, 2.0 Hz, 1 H), 7.36 (d, J = 8.8 Hz, 1 H), 7.25 (s, 1 H), 3.87 (s, 3H).

As the paragraph descriping shows that 525593-33-3 is playing an increasingly important role.

Reference：
Patent; PFIZER INC.; SCHNUTE, Mark Edward; FLICK, Andrew Christopher; JONES, Peter; KAILA, Neelu; MENTE, Scot Richard; TRZUPEK, John David; VAZQUEZ, Michael L.; XING, Li; ZHANG, Liying; WENNERSTAL, Goran Mattias; ZAMARATSKI, Edouard; (82 pag.)WO2016/120850; (2016); 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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.525593-33-3,3-Bromo-5-nitroindole,as a common compound, the synthetic route is as follows.

To a stirred solution of 3-bromo-5-nitro-lH-indole (2) (100.0 g, 0.414 mol) in DMF (1 L) was added NaH (19.9 g, 0.829 mol) at 0 C and the solution was stirred for 0.5 h. Methyl iodide (87.7 g, 0.622 mol) was then added to the reaction mixture and the solution was stirred at RT for another 2 h. After completion of reaction the mixture was quenched with water and extracted with ethyl acetate. The organic extract was dried over anhydrous sodium sulphate, filtered and solvents evaporated from the filtrate under reduced pressure to obtain a crude, which was purified by column chromatography on silica gel (100-200 mesh), eluted with 10-15% gradient of EtOAc in pet-ether, to afford 3 -bromo-l -methyl-5 -nitro-lH- indole (101.0 g, 95%)., 525593-33-3

Big data shows that 525593-33-3 is playing an increasingly important role.

Reference：
Patent; COUNCIL OF SCIENTIFIC & INDUSTRIAL RESEARCH; SRIVARI, Chandrasekhar; MAINKAR, Prathama Satyendra; REDDY, Chada Raji; KOTAMRAJU, Srigiridhar; TOGAPUR, Pavan Kumar; MUPPIDI, Subbarao Mohan Venkata; SHARMA, Somesh; JHA, Ashok Kumar; ARUMUGAM, Prem Kumar; (27 pag.)WO2019/102488; (2019); 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