Category: 5192-23-4

5192-23-4, Chemistry is the science of change. But why do chemical reactions take place? Why do chemicals react with each other? The answer is in thermodynamics and kinetics.In a document type is Article, the author is Chen, Jinchun and a compound is mentioned, 5192-23-4, 4-Aminoindole, introducing its new discovery.

One-pot tandem synthesis of 2,3-unsubstituted indoles, an improved Leimgruber-Batchoindole synthesis

A concise, fast and efficient one-pot methodology has been developed for preparing 2,3-unsubstituted indoles from 2-nitrotoluenes and dimethylformamide dimethyl acetal. Compared with the classical Leimgruber-Batcho reaction, such a one-pot process simplified the operation procedures, generated less by-products and chemical residues, and resulted in higher overall yields in a shorter reaction time.

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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

5192-23-4, 4-Aminoindole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

4. To a solution of Compound 4 (500 mg, 2.57 mmol) in DCM (10 mL) were added 4- aminoindole (340 mg, 2.57 mmol), EDCI (1 g, 5.14 mmol) and DMAP (80 mg). The reaction mixture was stirred at RT overnight. TLC indicated reaction completion. The residue was treated with water and extracted with DCM. The organic extracts were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to give a crude oil. The crude product was purified by silica gel chromatography to afford Example 43 (200 mg, 25.2%). 1HNMR (CDCI3, 300 MHz) delta: 1.3-1.4 (d, 3 H), 2.6-3.0 (m, 2 H), 3.7-3.9 (m, 4 H), 6.8- 7.0 (m, 2 H), 7.2-7.5 (m, 5 H), 7.6-7.8 (m, 1H). 8.2-8.3 (m, 1 H). LC-MS: m/z= 309.3 (M+l) +.

5192-23-4, As the paragraph descriping shows that 5192-23-4 is playing an increasingly important role.

Reference£º
Patent; FORGE LIFE SCIENCE, LLC; REMISZEWSKI, Stacy; KOYUNCU, Emre; SUN, Qun; CHIANG, Lillian; (133 pag.)WO2016/77240; (2016); A2;,
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

5192-23-4, 4-Aminoindole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

EXAMPLE 79 N-(3,4-dichlorobenzyl)-N’-1H-indol-4-ylurea 4-Aminoindole (0.13 g, 1 mmol) in THF (3 mL) was treated with 1,2-dichloro-4-(isocyanatomethyl)benzene (0.22 g, 1.1 mmol) for 3 h at ambient temperature. Hexane was added to the reaction mixture to precipitate 0.25 g of the title compound as a tan solid. mp 201 C.; 1H NMR (300 MHz, DMSO-d6) delta 4.23 (d, 2H), 6.36 (s, 1H), 6.54 (t, 1H), 7.0 (dd, 1H), 7.25 (m, 2H), 7.30 (d, 2H), 7.45 (d, 1H), 7.6 (m, 2H), 8.31 (s, 1H), 10.87 (s, 1H) MS (DCI+) m/z 336 (M+H); Anal. Calcd. For C16H13N3Cl2O: C, 57.50; H, 3.92; N, 12.57. Found: C, 56.94, H, 3.68; N, 11.97., 5192-23-4

5192-23-4 4-Aminoindole 583431, aindole-building-block compound, is more and more widely used in various fields.

Reference£º
Patent; Abbott Laboratories; US6933311; (2005); B2;,
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

5192-23-4, 4-Aminoindole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

EXAMPLE 19. N-(3-(9H-PURGammaN-6-YL)PYRIDGammaN-2-YL)- 1H-LNDOL-4-AMGammaNE [00165] 6-(2-Fluoropyridin-3-yl)-9-(tetrahydro-2H-pyran-2-yl)-9H-purine (115.0 mg, 0.3842 mmol) and lH-indol-4-amine (Aldrich, St. Louis, MO, 70.7 mg, 0.535 mmol) were suspended in EtOH (1.8 mL) and aqueous hydrochoric acid (5.0 M, 0.090 ml, 0.45 mmol) was added. The flask was fitted with a reflux condenser and placed in a preheated oil bath (100 0C), and the reaction was stirred for 3 hours. Then, the reaction was cooled to room temperature and diluted with DCM, 2 N ammonia in MeOH, EtOH, and MeOH and concentrated. The residue was treated with MeOH and filtered. Neither the filtrate nor the solid contained pure material, so they were combined, concentrated, treated with DMF, and filtered. The filtrate was concentrated and purified on HPLC (10% to 100% MeCN / water with 0.1% TFA over 30 minutes with a total flow rate of 100 mL/min). The fractions with product were collected, concentrated, and filtered through a silica gel plug (about 1 inch, 50: 1 DCM / 2 N ammonia in MeOH to 20: 1 DCM / 2 N ammonia in MeOH to 5: 1 DCM / 2 N ammonia in MeOH) to afford N-(3-(9H-purin-6-yl)pyridin-2-yl)-lH-indol-4-amine (6.9 mg, 5% yield). MS (ESI pos. ion) m/z: 328, (M+H)+. 1H NMR (d6-DMSO, 400 MHz) delta 12.90 (s, IH), 11.16 (s, IH), 9.87 (d, J = 7.82 Hz, IH), 9.24 (s, IH), 8.73 (s, IH), 8.43 (dd, J = 4.69 Hz, 1.96 Hz, IH), 8.28 (dd, J = 4.6 Hz, 3.81 Hz, IH), 7.38 – 7.35 (m, IH), 7.09 (s, IH), 7.08 – 7.06 (m, IH), 7.04 (dd, J = 7.82 Hz, 4.69 Hz, IH), 6.79 – 6.76 (m, IH)., 5192-23-4

The synthetic route of 5192-23-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; AMGEN INC.; ANDREWS, Kristin; BO, Yunxin, Y.; BOOKER, Shon; CEE, Victor, J.; D’ANGELO, Noel; HERBERICH, Bradley, J.; HONG, Fang-Tsao; JACKSON, Claire, L., M.; LANMAN, Brian, A.; LIAO, Hongyu; LIU, Longbin; NISHIMURA, Nobuko; NORMAN, Mark, H.; PETTUS, Liping, H.; REED, Anthony, B.; SMITH, Adrian, L.; TADESSE, Seifu; TAMAYO, Nuria, A.; WU, Bin; WURZ, Ryan; YANG, Kevin; WO2010/126895; (2010); 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

5192-23-4, 4-Aminoindole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a stirred solution of 4-chloro-5-[3-(2-chloroethoxy)phenyl]-nicotinonitrile (200 mg, 0.68 mmol), 4-aminoindole (135 mg, 1 mmol), DavePhos (80 mg, 0.20 mmol), and K3PO4 (216 mg, 1 mmol) in 4 mL anhydrous ethylene glycol dimethyl ether was added Pd2(dba)3 (62 mg, 0.07 mmol). The mixture was heated at 90 C. for 2 h then cooled, filtered through celite, concentrated in vacuo, and purified by flash chromatography on silica gel eluting with a gradient of 5-50% MeOH in CH2Cl2 to yield 155 mg (59% yield) of 5-[3-(2-chloroethoxy)phenyl]-4-(1H-indol-4-ylamino)-nicotinonitrile 165 as a tan solid. MS: 389.1 (M+H), HPLC retention time: 9.60 min.(a)., 5192-23-4

The synthetic route of 5192-23-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Cole, Derek Cecil; Boschelli, Diane Harris; Wang, Yanong Daniel; Asselin, Magda; Joseph-McCarthy, Diane Marie; Prashad, Amarnauth Shastrie; Wissner, Allan; Dushin, Russell; Wu, Biqi; Tumey, Lawrence Nathan; Niu, Chuan S.; Chen, Joan; US2007/287708; (2007); 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.5192-23-4,4-Aminoindole,as a common compound, the synthetic route is as follows.

General procedure: The solution of isatin (380 mumol), 1H-indole-4-amine (380 mumol, 1.0 equiv), and Meldrum’s acid (380 mumol, 1.0 equiv) in DMF (4.0 ml) was heated to 120 C for 2 h. The reaction mixture was cooled down to room temperature and concentrated to remove the solvents. The crude residue was subjected to reverse phase preparative HPLC to provide pure products., 5192-23-4

As the paragraph descriping shows that 5192-23-4 is playing an increasingly important role.

Reference£º
Article; Zou, Bin; Chen, Chun; Leong, Seh Yong; Ding, Mei; Smith, Paul W.; Tetrahedron; vol. 70; 3; (2014); p. 578 – 582;,
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