Category: 5192-03-0

5192-03-0, 1H-Indol-5-amine is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution 5-aminoindole (1.0 g, 7.6 mmol) in 100 mL of EtOAc was added di- tert-butyldicarbonate (4.1 g. 19 mmol). The mixture was stirred at ambient temperature for 24 hours and then was quenched with 20 mL H2O. The layers were separated and the aqueous layer was extracted 3 X 10 mL of EtOAc. The combined organic extracts were dried over anhydrous Na2SO4, filtered, concentrated under reduced pressure and purified via flash column chromatography (SiO2, 50% hexanes in EtOAc) to provide the title compound (1.8 g, 7.7 mmol, ->100% yield). MS (DCI/NH3) m/z 233 (M+H)+., 5192-03-0

The synthetic route of 5192-03-0 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; ABBOTT LABORATORIES; WO2006/69196; (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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.5192-03-0,1H-Indol-5-amine,as a common compound, the synthetic route is as follows.

General procedure: General procedure (10): To a solution of aminoindole (1.0 equiv) and triethylamine (3.6 equiv) in dichloromethane (10 ml_ for 1.182 mmol of starting material), acetyl chloride (1.2 equiv) was added. The reaction was stirred at room temperature for 3 h. The mixture was poured into water and extracted with dichloromethane 3 times. The combined organic layer was washed with brine, dried over anhydrous sodium sulphate and concentrated in vacuo. Purification by flash silica gel column chromatography afforded the indole-acetamide product. Intermediate 17 A/-(1/-/-indol-5-yl)acetamide Intermediate 17 (177 mg, 1.016 mmol) was prepared as a clear oil from Intermediate 16 (156 mg, 1.182 mmol) according to general procedure (10) using 7:3 hexane/ethyl acetate as the eluent for flash silica gel column chromatography. Yield: 85%. 1H NMR (400 MHz, CDCI3) delta 8.27 (bs, 1 H), 7.80 (s, 1 H), 7.30 (d, J = 8.5 Hz, 2H), 7.20 (dd, J = 8.8, 2.0 Hz, 2H), 6.50 (s, 1 H), 2.18 (s, 3H)., 5192-03-0

The synthetic route of 5192-03-0 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; NATIONAL UNIVERSITY OF SINGAPORE; LEE, Sang Hyun; DYMOCK, Brian William; KITAGAWA, Mayumi; SEE, Cheng Shang; (178 pag.)WO2016/200339; (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.5192-03-0,1H-Indol-5-amine,as a common compound, the synthetic route is as follows.

Intermediate-1: N-(lH-indol-5-yl)pivalamideTo a stirred solution of 5-Indole amine (0.6 g, 4.54 mmol) in anhydrous dichloromethane (15 mL), triethylamine (1.3 mL, 9.0 mmol) and pivaloyl chloride (0.45 mL, 5.4 mmol) were added and stirred at room temperature for 2 h. The reaction mixture was diluted with water; the organic layer was separated and concentrated in vacuo. The resultant residue was purified by flash column chromatography to give N-(lH-indol-5-yl)pivalamide (0.88g, 89%); MS: 217.0 (M+l).

5192-03-0, As the paragraph descriping shows that 5192-03-0 is playing an increasingly important role.

Reference：
Patent; LUPIN LIMITED; THOTAPALLY, Rajesh; KACHI, Onkar, Gangaram; RODGE, Atish, Harishchandra; PATHAK, Ashok, Bhau; KARDILE, Bhavana, Shrirang; SINDKHEDKAR, Milind, Dattatraya; PALLE, Venkata, P.; KAMBOJ, Rajender, Kumar; WO2012/69917; (2012); 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

5192-03-0, 1H-Indol-5-amine is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a stirred solution of lH-indol-5 -amine (0.6 g, 4.54 mmol) in dichloromethane (15 mL), was added triethylamine (1.3 mL, 9.08 mmol) and a solution of tert butyl carbonyl chloride (0.46 mL, 5.44 mmol) in dichloromethane (2 mL) at 0C and stirred for 1.5 h. The reaction mixture was diluted with dichloromethane and washed with water, and the organic phase was dried over anhydrous Na2S04 and concentrated in vacuo. The resultant residue was purified and yielded N-(lH-indol-5-yl)pivalamide (0.88 g, 89%). MS: 217 (M+1); 1H NMR (400 MHz, DMSO-d6) delta; 1.22 (s, 9H), 6.34-6.35 (m, 1H), 7.20 (dd, J = 8.8, 2.0 Hz, 1H), 7.26-7.29 (m, 2H), 7.77 (d, J= 2.0 Hz, 1H), 9.00 (s, 1H), 10.96 (s, 1H).

5192-03-0, 5192-03-0 1H-Indol-5-amine 78867, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; LUPIN LIMITED; THOTAPALLY, Rajesh; PATHAK, Ashok, Bhau; KARDILE, Bhavana, Shrirang; SINDKHEDKAR, Milind, Dattatraya; PALLE, Venkata, P.; KAMBOJ, Rajender, Kumar; WO2012/25811; (2012); 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.5192-03-0,1H-Indol-5-amine,as a common compound, the synthetic route is as follows.

A mixture of 2-amino-4,6-dichloropyrimidine (1.64 g, 10 mmol), 5-aminoindole (1.32 g, 10 mmol), diisopropylethylamine (5.23 ml, 30 mmol) and N,N-dimethylformamide (30 ml) was heated at 60C and stirred overnight under nitrogen atmosphere. The reaction mixture was partitioned between ethyl acetate and water after cooled to room temperature; and the organic layer was washed with water and brine, and dried over anhydrous sodium sulfate. The solvent was distilled off; the obtained residue was dissolved in tetrahydrofuran (100 ml); 10% Palladium on carbon (50% wet, 1.0 g) was added thereto under nitrogen atmosphere; and the reaction mixture was stirred for 4 days under hydrogen atmosphere at atmospheric pressure. The reaction system was purged with nitrogen; the catalyst was filtered off; the filtrate was concentrated under reduced pressure; the residue was purified by NH silica gel column chromatography (eluent; ethyl acetate: methanol = 95: 5); diethyl ether was added to the residue to crystallize; and the crystals were filtered off, and dried under aeration to yield the title compound (852 mg, 3.8 mmol, 38%) as pale brown crystals. 1H-NMR Spectrum (DMSO-d6) delta (ppm): 5.89 (1H, d, J=5.6 Hz), 5.99 (2H, brs), 6.34 (1H, s), 7.12 (1H, d, J=8.4 Hz), 7.20-7.40 (2H, m), 7.70 (1H, d, J=5.6 Hz), 7.79 (1H, s), 8.73 (1H, s), 10.95 (1H, s).

5192-03-0, 5192-03-0 1H-Indol-5-amine 78867, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; Eisai Co., Ltd.; EP1522540; (2005); 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.5192-03-0,1H-Indol-5-amine,as a common compound, the synthetic route is as follows.

A solution of 5-amino indole (2 g, 15.2 mmol) and di-tert-butyl dicarbonate (3.49 g. 15.2 mmol) in dichloromethane (20 ml) was stirred at ambient temperature overnight. The reaction mixture was concentrated under reduced pressure to yield crude (1H-indol-5-yl)-carbamic acid tert-butyl ester (3.47 g) which was used in the next step without further purification. MS: 250.3 (M+NH4)+., 5192-03-0

The synthetic route of 5192-03-0 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Ackermann, Jean; Aebi, Johannes; Binggeli, Alfred; Grether, Uwe; Hirth, Georges; Kuhn, Bernd; Maerki, Hans-Peter; Meyer, Markus; Mohr, Peter; Wright, Matthew Blake; US2005/96353; (2005); 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.5192-03-0,1H-Indol-5-amine,as a common compound, the synthetic route is as follows.

To a stirred suspension of 3,5-dibromopyrazin-2-amine (3.48 g, 13.7 mmol) and IH- indol-5 -amine (2.00 g, 15.0 mmol) in EtOH (3.5 mL) was added diisopropylethylamine [DIEA] (2.60 mL, 15.0 mmol). The resulting mixture was stirred for 48 hr at 800C, after which it was partitioned between EtOAc and H2O. The organic layer was separated, after which it was washed with brine, dried over Na2SO4, filtered, and evaporated in vacuo to yield a residue that was purified via silica gel chromatography eluting with 1: 1 EtOAc :hexanes to yield the title compound (1.75 g, 42%) as a red/brown solid. 1H NMR (DMSO- d6, 300 MHz): delta 10.98 (s, IH), 8.22 (s, IH), 7.83 (s, IH), 7.31-7.28 (m, 3H), 7.19 (d, / = 8.7 Hz, IH), 6.43 (s, 2H), 6.36 (s, IH); HPLC retention time: 2.07 minutes; MS ESI (m/z): 304.2/306.2 (M+l)+, calc. 303, 5192-03-0

The synthetic route of 5192-03-0 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; UNIVERSITY OF ROCHESTER; GELBARD, Harris, A.; DEWHURST, Stephen; GOODFELLOW, Val, S.; WIEMANN, Torsten; WO2010/68483; (2010); 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