Category: 15903-94-3

15903-94-3, 6-(Benzyloxy)-1H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Procedure F: Deprotection of the benzyloxy group and reduction of the alpha,beta- unsaturated system. Method I: To a solution of an alpha,beta-unsaturated ester/acid/amide or/and compounds protected with a benzyl group (6.72 mmol) in EtOH (50 mL) was added 10percent Pd/C (0.16 g) and HC02NH4 (67 mmol). The mixture was refluxed for 1 h. The catalyst was removed by filtration through celite and concentrated to give the product.6-Hydroxyindole. 6-Hydroxyindole was prepared from 6-benzyloxyindole by procedure F (Methods I or II), was isolated by chromatography eluted with EtOAc- hexane (1 : 1) to give white solid in 66percent yield, mp 123- 125 ¡ãC [128-129 ¡ãC]. 1H-NMR (300 MHz, CDCI3) ppm delta 8.51 (bs, 1H, H-1), 7.41 (d, J = 8.8 Etazeta, IotaEta, H-4), 6.94 (t, J = 2.9 Hz, 1H, H-2), 6.80 (d, J = 2.2 Hz, 1H, H-7), 6.71 (dd, J = 8.8, 2.2 Hz, 1H, H-5), 6.38 (ddd, J = 2.9, 1.5, 0.7 Hz, 1H, H-3); 13C-NMR (75 MHz, CDC13) ppm delta 152.19, 136.78, 123.09, 121.90, 120.87, 109.76 (C-7)., 15903-94-3

15903-94-3 6-(Benzyloxy)-1H-indole 260804, aindole-building-block compound, is more and more widely used in various fields.

Reference£º
Patent; YISSUM RESEARCH DEVELOPMENT COMPANY OF THE HEBREW UNIVERSITY OF JERUSALEM LTD; BAR ILAN UNIVERSITY; NUDELMAN, Abraham; WEINSTOCK-ROSIN, Marta; WO2013/150529; (2013); 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

15903-94-3, 6-(Benzyloxy)-1H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Procedure F: Deprotection of the benzyloxy group and reduction of the alpha,beta- unsaturated system. Method I: To a solution of an alpha,beta-unsaturated ester/acid/amide or/and compounds protected with a benzyl group (6.72 mmol) in EtOH (50 mL) was added 10percent Pd/C (0.16 g) and HC02NH4 (67 mmol). The mixture was refluxed for 1 h. The catalyst was removed by filtration through celite and concentrated to give the product.6-Hydroxyindole. 6-Hydroxyindole was prepared from 6-benzyloxyindole by procedure F (Methods I or II), was isolated by chromatography eluted with EtOAc- hexane (1 : 1) to give white solid in 66percent yield, mp 123- 125 ¡ãC [128-129 ¡ãC]. 1H-NMR (300 MHz, CDCI3) ppm delta 8.51 (bs, 1H, H-1), 7.41 (d, J = 8.8 Etazeta, IotaEta, H-4), 6.94 (t, J = 2.9 Hz, 1H, H-2), 6.80 (d, J = 2.2 Hz, 1H, H-7), 6.71 (dd, J = 8.8, 2.2 Hz, 1H, H-5), 6.38 (ddd, J = 2.9, 1.5, 0.7 Hz, 1H, H-3); 13C-NMR (75 MHz, CDC13) ppm delta 152.19, 136.78, 123.09, 121.90, 120.87, 109.76 (C-7)., 15903-94-3

15903-94-3 6-(Benzyloxy)-1H-indole 260804, aindole-building-block compound, is more and more widely used in various fields.

Reference£º
Patent; YISSUM RESEARCH DEVELOPMENT COMPANY OF THE HEBREW UNIVERSITY OF JERUSALEM LTD; BAR ILAN UNIVERSITY; NUDELMAN, Abraham; WEINSTOCK-ROSIN, Marta; WO2013/150529; (2013); 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.15903-94-3,6-(Benzyloxy)-1H-indole,as a common compound, the synthetic route is as follows.

To a stirred, cooled [(10OC)] suspension of sodium hydride (80.7 g of a 60% dispersion in mineral oil, 2.02 mol) in anhydrous THF (1.9 L) was added a solution of 6- benzyloxyindole (375 g, 1.68 mol) in anhydrous THF (1.9 L) keeping the temperature below [25OC.] After 2 h at 10C, propylene oxide (140 mL, 2.0 mol) was added dropwise keeping the temperature below [25OC.] After 48 h at 10C, propylene oxide (71 mL, 1.0 mol) was added. After 96 h at 10 oC, saturated aqueous potassium dihydrogenphosphate (3.8 L) and ethyl acetate (3.8 L) were carefully added, the layers were separated and the aqueous solution was extracted with 3.8 L of ethyl acetate. The combined organic extracts were dried over sodium sulfate and concentrated in vacuo to yield a solid (520 g, 110%, contains mineral oil).

15903-94-3, 15903-94-3 6-(Benzyloxy)-1H-indole 260804, aindole-building-block compound, is more and more widely used in various fields.

Reference£º
Patent; ALCON, INC.; WO2003/101379; (2003); 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.15903-94-3,6-(Benzyloxy)-1H-indole,as a common compound, the synthetic route is as follows.

General procedure: A test tube containing 7-nitro-3-phenyl-2H-benzo[b][1,4]oxazin-2-one (0.1 mmol), indole (0.1 mmol) and chiral phosphoric acid (8.7 mg, 0.01 mmol) was added 1.0 mL acetone, then the mixture was stirred at room temperature until the reaction was complete (monitored by TLC). Finally, the reaction mixture was directly poured to the column chromatograpy, using petroleum ether:ether acetate (5:1) as eluent to afford product., 15903-94-3

As the paragraph descriping shows that 15903-94-3 is playing an increasingly important role.

Reference£º
Article; Zhao, Yunlong; Wang, Longsheng; Zhao, Junling; Tetrahedron Letters; vol. 58; 3; (2017); p. 213 – 217;,
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

15903-94-3, 6-(Benzyloxy)-1H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: General procedure for I catalyzed cascade Michael addition-hemiketalization reaction and the subsequent BF3¡¤Et2O promoted Friedel-Crafts alkylation reaction To a stirred solution of catalyst I (15 mol percent) and 2-((E)-2-nitrovinyl)phenols (8, 1 mmol) in toluene (2.5 mL), acetone (5 equiv, 5 mmol) was added. The resulting solution was stirred at 25 ¡ãC. After the reaction was complete (monitored by TLC), the reaction mixture was concentrated under reduced pressure and the crude product was purified by column chromatography on silica gel (200-300 mesh, PE/EtOAc=10/1) to afford the desired lactol intermediates 9 or open-chain compound 12. To a mixture of the obtained lactols 9 and indoles (10, 1.2 equiv) in acetonitrile (1 mL), BF3¡¤OEt2 (60 mol percent) was added portionwise at 25 ¡ãC. The resulting mixture was stirred at the same temperature for 10 h. The reaction mixture was concentrated in vacuo and the crude products were purified by column chromatography on silica gel (200-300 mesh, PE/EtOAc=10/1) to afford the desired 2-indolylchromanes 11. The title compounds were fully characterized by 1H NMR, 13C NMR, HRMS and specific rotation data. The enantiomeric excess of the pure products was determined by HPLC analysis using a chiral stationary phase.

15903-94-3, As the paragraph descriping shows that 15903-94-3 is playing an increasingly important role.

Reference£º
Article; Pan, Jianping; Wang, Yuehua; Chen, Shanren; Zhang, Xueqin; Wang, Youming; Zhou, Zhenghong; Tetrahedron; vol. 72; 1; (2016); p. 240 – 246;,
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

15903-94-3, 6-(Benzyloxy)-1H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

6-Benzyloxyindole (2) (2.00 g, 8.96 mmol), tetrahydrofuran (2.64 mL) and toluene (15.2 mL) were placed in a 50 mL three-necked flask equipped with a magnetic stirrer, a Dimroth condenser and a thermometer under nitrogen atmosphere. The mixture was warmed up to 38¡ãC, and 0.90 M dibutyl magnesium chloride/heptane (4.96 mL, 4.47 mmol) wherein the heptane contained a mixture of di(n-butyl)magnesium, di(sec-butyl)magnesium and (n-butyl)(sec-butyl)magnesium was added over 10 minutes, and the mixture was stirred at 55 ¡ãC to 60¡ãC for one hour. N-Methyl-1,2-dichloromaleimide (730 mg, 4.06 mmol) was dissolved in toluene (4.4 mL), and the solution was added to the above mixture over 10 minutes, and the container of the N-methyl-1,2-dichloromaleimide was washed with toluene (1 mL). After addition of the washing, the mixture was heated up to 55 ¡ãC to 60 ¡ãC, stirred at 55 ¡ãC to 60¡ãC to give a solid, which was dissolved homogenously by addition of tetrahydrofuran (1.5 mL). The solution was stirred at 55¡ãC to 60¡ãC for 30 minutes, further heated up to 98 ¡ãC to 100 ¡ãC, stirred at 98¡ãC to 100¡ãC for 12 hours, allowed to stand for cooling to room temperature and stirred overnight. After the reaction mixture being heated up to 90¡ãC, 13 percent aqueous ammonium chloride (17 mL) was added to the reaction mixture, and the mixture was cooled down to room temperature to give a suspension, which was filtered to give a red solid, which was washed successively with toluene (20 mL), toluene-water (mixing ratio of 1:1, 20 mL) and methanol (20 mL x 2). The solid was dried in vacuo overnight at room temperature to give the objective bis-indole (3) in 82 percent yield (crop 1.85 g).1H-NMR (500MHz, DMSO-d6, deltappm): 11.50 (s, 2H), 7.63 (d, J= 2.3 Hz, 2H), 7.42 (d, J=7.3 Hz, 2H), 7.37 (dd, J= 7.3, 7.3 Hz, 2H), 7.30 (dd, J= 7.3, 7.3 Hz, 2H), 6.97 (d, J = 2.1 Hz, 2H), 6.72 (d, J= 8.8 Hz, 2H), 6.41 (dd, J= 2.1, 8.8 Hz, 2H), 5.04 (s, 4H), 3.03 (s, 3H)13C-NMR (126MHz, DMSO-d6, deltappm): 172.2, 155.0, 137.7, 137.1, 128.7, 128.5, 128.1, 128.0, 127.1, 122.0, 120.1, 110.4, 106.1, 96.3, 69.7, 24.3 M.p. ca. 240¡ãC (decomp.)

15903-94-3, The synthetic route of 15903-94-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BANYU PHARMACEUTICAL CO., LTD.; EP1541582; (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