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

4,6-Dichloropyrimidine (5.89 g, 40 mmol), 5-aminoindole (6.27 g, 47 mmol) and N,N-diisopropylethylamine (20.6 ml, 0.12 mol) were dissolved in N-methylpyrrolidone (80 ml), and the reaction mixture was stirred at 50C for 2.5 hours. The reaction mixture was partitioned between ethyl acetate and water; the aqueous layer was subjected to re-extraction with ethyl acetate; and the combined organic layer was washed with brine, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure; a small amount of ethyl acetate was added to the residue to crystallize; and the crystals were filtered off, washed with diethyl ether, and dried under aeration to yield the title compound (3.70 g, 15 mmol, 38%) as white crystals. 1H-NMR Spectrum (DMSO-d6) delta (ppm): 6.42 (1H, m), 6.62 (1H, brs), 7.11 (1H, d, J=8.0 Hz), 7.35-7.40 (2H, m), 7.72 (1H, brs), 8.38 (1H, s), 9.68 (1H, s), 11.11 (1H, s)., 5192-03-0

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

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

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

DMSO (10 L, 11 kg), 2-amino-3,5-dibromopyrazine (1) (4.5 kg, 17.8 mol, 1 eq.), 5- amino indole (2) (3.06 kg, 23.15 mol, 1.3 eq.) and triethylamine (7.4 L, 5.4 kg, 53.36 mol, 3 eq.) were charged to a reactor. The reaction mixture was heated to 95C while agitated. After 12 hours, the heating was discontinued and the conversion was 88% of 2-amino-3,5-dibromopyrazine. The reaction was heated again to 95C and agitated for an additional 2.5 hours. There was no improvement in conversion. The reaction mixture was agitated at ambient temperature overnight. Triethylamine (3.5 kg) was removed under vacuum and the remaining reaction mixture was transferred to a stainless steel container from which it was charged into another reactor. Subsequently, 8.4 kg of 50% acetic acid (aq.) was introduced over a period of 20 minutes under agitation, followed by purified water (61 L) charged over a period time of 60 minutes. The slurry was then filtered and the isolated material was washed with 2 x 20 L of 1 % acetic acid (aq.). The isolated 3-bromo-N-3-(1H-indol-5-yl)-pyrazine-2,3-diamine) (3) was transferred to a drying cabinet and dried to invariable weight at 40±3C, (19 hours), to afford 4.36 kg, 14.34 mol, 81 % yield, with a purity of 96% by HPLC. The reaction temperature in the batch record was set to be 130-135C. However, at 95C the reaction mixture was at reflux., 5192-03-0

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

Reference：
Patent; AKINION PHARMACEUTICALS AB; LEHMANN, Fredrik; BREMBERG, Ulf; SOeLVER, Ellen; ERIKSSON BAJTNER, Johan; THORNQVIST OLTNER, Viveca; WO2013/89636; (2013); 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

Using procedure A: 2-Amino-3,5-dibromo-pyrazine (100 mg) and 5-aminoindole (200 mg) yielded 150 mg of a 1 :1 mixture of 5-aminoindole and the desired product MS m/z 303 [M + H]+ which was used without further purification or characterization.; Procedure A:General procedure for SNAgamma on 2-amino-3,5-dibromo-pyrazine2-Amino-3,5-dibromo-pyrazine, triethylamine (3 equiv) and the appropiate amine or alcohol (3 equiv) were dissolved in 4 mL water and the resulting mixture was heated to 195 0C for 1 hour. Water and ethyl acetate were added and the phases separated. The water phase was extracted once more with ethyl acetate. The combined organic phases were washed (water and brine) and concentrated to yield a crude mixture of product and unre- acted amine or alcohol. This crude mixture was used without further purification or characterization in the subsequent Suzuki reaction.

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

Reference：
Patent; BIOVITRUM AB (publ); WO2009/95399; (2009); 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

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

Preparation of 6-bromo-/V2-(lH-indol-5- l)pyrazine-2,3-diamine (Intermediate BB)[0323] To a stirred suspension of 3,5-dibromopyrazin-2-amine (3.48 g, 13.7 mmol) and H- 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 80C, after which it was partitioned between EtOAc and H20. The organic layer was separated, after which it was washed with brine, dried over Na2S04, 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-dtf, 300 MHz): delta 10.98 (s, 1H), 8.22 (s, 1H), 7.83 (s, 1H), 7.31-7.28 (m, 3H), 7.19 (d, J= 8.7 Hz, 1H), 6.43 (s, 2H), 6.36 (s, 1H); HPLC retention time: 2.07 minutes; MS ESI (m/z): 304.2/306.2 (M+l)+, calc. 303.

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; UNIVERSITY OF ROCHESTER; GELBARD, Harris, A.; DEWHURST, Stephen; GOODFELLOW, Val, S.; WIEMANN, Torsten; RAVULA, Satheesh, Babu; LOWETH, Colin, J.; WO2011/149950; (2011); 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

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.

Glacial acetic acid (1.3 mL, 22.7 mmol) and sodium triacetoxyborohydride (6.73 g, 31.7 mmol) were added to a solution of 5-aminoindole (3 g, 22.7 mmol), 4-oxo-piperidine-1-carboxylic acid tert-butyl ester (4.52 g, 22.7 mmol) in 1,2-dichloroethane (100 mL). The reaction mixture was stirred for 4 hours at room temperature; an aqueous solution of NaOH (1 M, 100 mL) was then added. The organic layer was separated, dried over MgSO4, filtered and evaporated under reduced pressure to give 6.9 g (96% yield) of 4-(1H-indol-5-ylamino)-piperidine-1-carboxylic acid tert-butyl ester as a black foam; this material was used without further purifications for the next step., 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; Iyer, Pravin; Lucas, Matthew C.; Schoenfeld, Ryan Craig; Weikert, Robert James; US2009/247568; (2009); 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

Intermediate-69: tert-Butyl lH-indol-5-ylcarbamate To a stirred solution lH-indol-5 -amine (0.5 g, 3.78 mmol) in dichloromethane (10 mL), triethylamine (0.95g, 9.4 mmol) and di-tert-butyl dicarbonate (0.908 g, 4.166 mmol) were added at 0C. The reaction contents were stirred at room temperature for 4 h. The reaction was quenched with water and the mixture was extracted with ethyl acetate. The organic layer was concentrated in vacuo and the residue was purified by flash column chromatography to give tert-butyl lH-indol-5-ylcarbamate (0.380 g, 43%); MS: 233.5 (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

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 lH-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 80C, after which it was partitioned between EtOAc and I0. The organic layer was separated, after which it was washed with brine, dried over Na2S04, 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. XH NMR (DMSO-i , 300 MHz): delta 10.98 (s, IH), 8.22 (s, IH), 7.83 (s, IH), 7.31-7.28 (m, 3H), 7.19 (d, J= 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, As the paragraph descriping shows that 5192-03-0 is playing an increasingly important role.

Reference：
Patent; UNIVERSITY OF ROCHESTER; BOARD OF REGENTS OF THE UNIVERSITY OF NEBRASKA; GELBARD, Harris A.; DEWHURST, Stephen; GENDELMAN, Howard E.; WO2014/85795; (2014); 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.

Example 16 (1-{4-[3-(4-Chloro-3-(trifluoromethyl)phenyl)ureido]-2-fluorophenyl}-1H-indol-5-yl)carbamic acid tert-butyl ester (Table 1, Compound No. 16) Step A Preparation of (1H-indole-5-yl)carbamic acid tert-Butyl ester [Show Image] In 100 mL of methanol, 2.64 g (20 mmol) of 5-aminoindole was dissolved, and 4.15 mL (30 mmol) of triethylamine and 5.23 g (24 mmol) of Boc2O were added thereto and the mixture solution was stirred at room temperature for six hours. The reaction solution was concentrated under reduced pressure, and the residue was partitioned with ethyl acetate (200 mL) and water (100 mL), and the organic layer was washed with a saturated sodium chloride solution. The organic layer was dried and then concentrated under reduced pressure, and the residue was partitioned between ethyl acetate (200 mL) and water (100 mL) and the organic layer was washed with a saturated sodium chloride solution. The organic layer was dried and then concentrated under reduced pressure, and the residue was purified by a silica gel column (Wako Gel C200: 300 g, n-hexane:ethyl acetate=4:1) to obtain 4.38 g (94%) of (1H-indol-5-yl)carbamic acid tert-butyl ester as a white solid. 1H-NMR (270 MHz, CDCl3) delta (ppm): 1.43(9H,s), 6.38 (1H, br.s), 6.29-6.33 (1H, m), 7.04 (1H, dd, J=2.3, 8.9 Hz), 7.19 (1H, s), 7.23 (1H, d, J=8.9 Hz), 7.61 (1H, br.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; CHUGAI SEIYAKU KABUSHIKI KAISHA; EP1724258; (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

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 of intermediate 16 (156?mg, 1.182?mmol, 1.0 equiv) and triethylamine (591?muL, 429?mg, 4.240?mmol, 3.6 equiv) in DCM (10?mL), acetyl chloride (101?muL, 111?mg, 1.418?mmol, 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 (7:3 hexane/ethyl acetate) afforded intermediate 7g as a clear oil (177?mg, 1.016?mmol). Yield: 85%. 1H NMR (400?MHz, CDCl3) delta 8.27 (bs, 1H), 7.80 (s, 1H), 7.30 (d, J?=?8.5?Hz, 2H), 7.20 (dd, J?=?8.8, 2.0?Hz, 2H), 6.50 (s, 1H), 2.18 (s, 3H).

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：
Article; See, Cheng Shang; Kitagawa, Mayumi; Liao, Pei-Ju; Lee, Kyung Hee; Wong, Jasmine; Lee, Sang Hyun; Dymock, Brian W.; European Journal of Medicinal Chemistry; vol. 156; (2018); p. 344 – 367;,
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

5-Aminoindole (100 mg, 0.757 mmol) was dissolved in acetonitrile (2 mL), and the solution was added with 1-(tert-butoxycarbonyl)-4-piperidinone (181 mg, 0.908 mmol), acetic acid (0.870 mL, 15.2 mmol) and sodium triacetoxyborohydride (160 mg, 0.755 mmol) little by little, followed by stirring at room temperature for 1 hour. The reaction mixture was added with water and sodium carbonate to adjust the pH to 9. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated to obtain 5-[1-(tert-butoxycarbonyl)-4-piperidylamino]indole (300 mg). 5-[1-(tert-butoxycarbonyl)-4-piperidylamino]indole APCI-MS m/z: 316 [M+H]+; 1H-NMR (CDCl3)delta(ppm): 1.21-1.42 (m, 2H), 1.47 (s, 9H), 2.03-2.14 (m, 2H), 2.86-2.98 (m, 2H), 3.43 (m, 1H), 3.97-4.13 (m, 2H), 6.39 (m, 1H), 6.62 (dd, J = 2.2, 8.6 Hz, 1H), 6.88 (d, J = 2.2 Hz, 1H), 7.13 (dd, J = 2.7, 2.8 Hz, 1H), 7.21 (d, J = 8.6 Hz, 1H), 7.96 (br s, 1H)., 5192-03-0

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

Reference：
Patent; Kyowa Hakko Kirin Co., Ltd.; EP2108642; (2009); 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