Indole Building Blocks

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.2380-84-9,1H-Indol-7-ol,as a common compound, the synthetic route is as follows.

[463] To a mixture of 7-hydroxyindole (4.5 g, 33.8 mmol) and THE (200 mL) was added triphenylphosphine (17.7 g, 67.7 mmol), diisopropyl azodicarboxylate (13.3 mL, 67.7 mmol) and 2- chloroethanol (4.5 mL, 67.1 mmol). After stirring at it overnight, the reaction mixture was concentrated in vacuo and the resulting residue was purified by flash column chromatography on silica gel (100% heptane to 10% EtOAc/heptane) to afford 7-(2-chloroethoxy)indole (B1) as a pale yellow oil.

2380-84-9, The synthetic route of 2380-84-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ARIAD PHARMACEUTICALS, INC.; HUANG, Wei-Sheng; LI, Feng; DALGARNO, David, C.; GONG, Yongjin; ISHCHENKO, Alexey, V.; KOHLMANN, Anna; SHAKESPEARE, William, C.; WEST, Angela, V.; XU, Yongjin; YOUNGSAYE, Willmen; ZHANG, Yun; ZHOU, Tianjun; ZHU, Xiaotian; (444 pag.)WO2015/175632; (2015); 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

487-89-8,487-89-8, Indole-3-carboxaldehyde is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of indole 3-carboxaldehyde (8y) (100 mmol) in ethanol (500 mL) at RT was added potassium hydroxide (1.1 equiv). The mixture was stuffed until total solubilization. The ethanol was completely removed in vacuum and the residual was dissolved in acetone (250 mL) followed by adding benzenesulfonyl chloride (1.1 equiv, 110 mmol). The reaction mixture was stuffed forhalf hour. The precipitate was filtered off and the filtrate was concentrated and recrystallized from methanol to give a white solid. Yield: 33%. ?H NMR (500 MHz, CDC13) oe 10.17 (s, 1 H), 8.25-8.39 (m, 2 H), 7.97-8.09 (m, 3 H), 7.69 (t, J= 7.33 Hz, 1 H), 7.59 (t, J= 7.5 Hz, 2 H), 7.39 -7.54 (m, 2 H). MS (ESI) calcd for C,5H,,N035 285.1, found 286.0 [M + Hf?.

487-89-8 Indole-3-carboxaldehyde 10256, aindole-building-block compound, is more and more widely used in various fields.

Reference£º
Patent; UNIVERSITY OF TENNESSEE RESEARCH FOUNDATION; WANG, Jin; CHEN, Jianjun; MILLER, Duane D.; LI, Wei; WO2014/138279; (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.16732-57-3,Ethyl 5-nitro-1H-indole-2-carboxylate,as a common compound, the synthetic route is as follows.

Commercially available ethyl 5-nitro-1H-indole-2-carboxylate (1.00 g, 4.27 mmol) of methanol (20 mL) solution Palladium-carbon (907 mg) in addition, stirred for three hours under a hydrogen atmosphere. Celite filtration reaction and be evaporated and the residue that obtained the title compound (876 mg, 100%).

16732-57-3, The synthetic route of 16732-57-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; DAINIPPON SUMITOMO PHARMA CO LTD; IKUMA, YOHEI; IWATA, MASAKADO; NAKAI, YOSHIO; (62 pag.)JP2015/13821; (2015); A;,
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.90271-86-6,5-Bromo-3-cyanoindole,as a common compound, the synthetic route is as follows.

90271-86-6, To a solution of 5-bromo-3-cyanoindole (2.0 g) in N,N-dimethylformamide (50 mL) were added cesium carbonate (7.4 g) and 4-fluorobenzoic acid ethyl ester (3.0 g), and this mixture was stirred at 80C for 48 hours. This reaction mixture was poured into water, and the precipitated solid was collected by filtration. This solid was washed with water, dried under reduced pressure at 50C to give the title compound (1.8 g).

As the paragraph descriping shows that 90271-86-6 is playing an increasingly important role.

Reference£º
Patent; Kissei Pharmaceutical Co., Ltd.; EP2133332; (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

169674-02-6, 4-Chloro-5-fluoro-1H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

a) A suspension of 0.11 g of sodium hydride dispersion in 15 ml of tetrahydrofuran was treated with 0.5 g of 4-chloro-5-fluoroindole at 0 and stirred at this temperature for 1 hour. After the addition of 0.4 ml of (R)-methyloxirane the reaction mixture was stirred at room temperature for 48 hours and subsequently treated with water. The mixture was diluted with ether, washed with water and with saturated sodium chloride solution and the organic phase was dried over sodium sulfate. After removal of the solvent the residue was chromatographed over 30 g of silica gel with toluene-ethyl acetate (33:1). There was obtained 0.5 g (74.5%) of (R)-1-(4-chloro-5-fluoro-indol-1-yl)-propan-2-ol as a yellow oil., 169674-02-6

The synthetic route of 169674-02-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Hoffmann-La Roche Inc.; US5494928; (1996); A;,
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

6146-52-7,6146-52-7, 5-Nitroindole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

5-(Piperazin-1-yl)-1H-indole; A mixture of 5-nitro-1H-indole (34 g), palladium (5 wt %, dry basis) on activated carbon (2.5 g) and ethyl acetate was shaken at room temperature for 1.5 h under 3 atmospheres of hydrogen. The mixture was filtered, and the solvent was removed in vacuo to yield a solid (28 g), which was dissolved in tetrahydrofuran (400 mL). This solution was added to a boiling mixture of N-benzyliminodiacetic acid (54.4 g) and 1,1′-carbonyldiimidazole (82.4 g) in tetrahydrofuran (1100 mL), and the resulting mixture was boiled under reflux for 3 h. The mixture was filtered and concentrated in vacuo. The residue was purified by flash chromatography on silicagel (eluent: ethyl acetate/triethylamine 100:4) to give a solid (57.5 g), which subsequently was suspended in tetrahydrofuran (300 mL) and added to alane in tetrahydrofuran (500 mL) at 5-16 C. The alane was prepared from lithium aluminium hydride (25 g) and 96% sulphuric acid (32.3 g). The mixture was stirred at 5 C. for 45 min and subsequently quenched by addition of water (50 mL), 15% aqueous sodium hydroxide solution (25 mL) and water (125 mL). The mixture was dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by flash chromatography on silicagel (eluent: ethyl acetate) to give a brown oily compound (44.9 g), which subsequently was dissolved in methanol (1000 mL). Ammonium formate (150 g) and palladium (5 wt %, dry basis) on activated carbon (12 g) was added, and the mixture was boiled under reflux for 45 min, cooled, filtered and concentrated in vacuo. The residue was dissolved in tetrahydrofuran/ethyl acetate and poured onto brine. Concentrated aqueous ammonia solution was added to the mixture under cooling to give an alkaline reaction mixture. The two phases were separated, and the aqueous phase was extracted twice with tetrahydrofuran/ethyl acetate. The combined organic phases were washed with brine, dried (MgSO4) and concentrated in vacuo. The residue was precipitated from tetrahydrofuran/heptane to give the title compound (17.3 g).

As the paragraph descriping shows that 6146-52-7 is playing an increasingly important role.

Reference£º
Patent; Bang-Andersen, Benny; Larsen, Krestian; Mork, Niels; US2007/43058; (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

40913-43-7, 1-Ethyl-1H-indole-2-carbaldehyde is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,40913-43-7

In two equal batches, 1,1 -dimethyl ethyl {(3R)-l-[(4-{[3-({[(9H-fluoren-9- ylmethyl)oxy]carbonyl}amino)propyl]amino}-3-nitrophenyl)carbonyl]-3- piperidinyl} carbamate (6 g, 9.32 mmol), l-ethyl-lH-indole-2-carbaldehyde (7.844 g, 27.96 mmol) and sodium hydrosulfite (4.868 g, 27.96 mmol) were combined in ethanol (40 mL) and water (20 mL) and heated in a Biotage Initiator microwave using initial high absorbtion setting to 100 C for 6 h. The reaction mixtures were combined and then partitioned between DCM (150 mL) and water (150 mL). The ethanol from the reaction mixture led to poor separation of the two layers, so the whole mixture was evaporated under vacuum – to the point where it was assumed most of the ethanol had evaporated and only the aqueous layer remained. The aqueous layer was then extracted with DCM (3 x 100 mL). The organics were combined, dried using a hydrophobic frit and evaporated under vacuum. The sample was loaded in dichlorom ethane and purified by Biotage SP4 (2 x SNAP 100 g silica) using a gradient of 50-100% cyclohexane-ethyl acetate. The appropriate fractions were combined and evaporated under vacuum to give the required product 1, 1 -dimethyl ethyl [(3R)-l-({2-(l- ethyl- 1 H-indol-2-yl)- 1 – [3 -( { [(9H-fluoren-9-ylmethyl)oxy] carbonyl } amino)propyl] – 1 H- benzimidazol-5-yl}carbonyl)-3-piperidinyl]carbamate (1.83 g, 2.386 mmol, 51.2 % yield) as an off- white foam.LCMS (Method B): Rt 1.37 min, MH+ 767.

40913-43-7 1-Ethyl-1H-indole-2-carbaldehyde 13693148, aindole-building-block compound, is more and more widely used in various fields.

Reference£º
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; AMANS, Dominique; ATKINSON, Stephen, John; BARKER, Michael, David; CAMPBELL, Matthew; DIALLO, Hawa; DOUAULT, Clement; GARTON, Neil, Stuart; LIDDLE, John; RENAUX, Jessica, Fanny; SHEPPARD, Robert, John; WALKER, Ann, Louise; WELLAWAY, Christopher, Roland; WILSON, David, Matthew; (284 pag.)WO2016/185279; (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.80360-20-9,1-(Phenylsulfonyl)-1H-indole-3-carbaldehyde,as a common compound, the synthetic route is as follows.

A solution of chlorotitanium (IV) triethoxide (22.5 g, 103 mmol, 1.05 equiv, Holoway, H. Chem. Ind. 1962, 3, 214) in dichloromethane (69 mL) was added via cannula to a solution of ethyl 2-((S,2S,5S)-2-hydroxypinan-3-imino)glybioncin C (E2-11, 24.8 g, 97.8 mmol, 1 equiv, (a) Oguri, T.; Kaway, N.; Yamada, S. Chem. Pharm. Bull. 1978, 26, 803. (b) Solladi-Cavallo, A.; Simon, M. C. Tetrahedron Lett. 1989, 30, 6011. (c) Solladi-Cavallo, A.; Simon-Wermeister, M. C.; Schwarz, J. Organometallics 1993, 12, 3743) in dichloromethane (300 mL) at 0 C. A fine powder of 1-(phenylsulfonyl)-1H-indole-3-carbaldehyde (E2-10, 29.3 g, 103 mmol, 1.05 equiv, Wenkert, E.; Moeller, P. D. R.; Piettre, S. R. J. Am. Chem. Soc. 1988, 110, 7188) was then added as a solid to the reaction mixture. Triethylamine (27.3 mL, 196 mmol, 2.00 equiv) was subsequently added dropwise via syringe and the reaction mixture was stirred at 0 C. After 21 h, brine (1 L) at 0 C. was added to the reaction mixture and the resulting bilayer suspension was filtered through Celite. The organic layer was separated, and the aqueous layer was extracted with dichloromethane (2¡Á300 mL). The combined organic layers were dried over anhydrous sodium sulfate, were filtered, and were concentrated under reduced pressure. The resulting orange foam was purified by flash column chromatography on silica gel (eluent: gradient, 30?50% ethyl acetate in hexanes) to provide an inseparable mixture of diastereomeric aldol products (42.5 g, 80.6%) as a yellow foam. In some embodiments, the aldol products were highly prone to degradation through a retro-aldol pathway; thus, the mixture of diastereomers was quickly isolated and immediately used in the subsequent reaction. Structural assignments were made using additional information from gCOSY, HSQC, and gHMBC experiments. (1135) 1H NMR (600 MHz, CDCl3, 20 C.; only the peaks corresponding to the major diastereomer are tabulated): delta 7.96 (d, J=8.3, 1H, C8H), 7.86 (d, J=8.6, 2H, SO2Ph-o-H), 7.71 (s, 1H, C2H), 7.67 (d, J=7.8, 1H, C8H), 7.49 (t, J=7.6, 1H, SO2Ph-p-H), 7.39 (app-t, J=8.1, 2H, SO2Ph-m-H), 7.29 (app-t, J=7.3, 1H, C7H), 7.23 (app-t, J=7.2, 1H, C6H), 5.49 (d, J=6.9, 1H, C12H), 4.46 (d, J=6.9, 1H, C11H), 4.11-3.99 (m, 2H, CO2CH2CH3), 3.90 (br-s, 1H, C12OH), 2.42 (dd, J=2.0, 17.7, 1H, C16Ha), 2.19 (dd, J=2.7, 18.0, 1H, C16Hb), 2.11-2.05 (m, 1H, C18Ha), 2.00 (br-s, 1H, C20OH), 1.89 (app-t, J=5.8, 1H, C19H), 1.87-1.83 (m, 1H, C17H), 1.42 (s, 3H, C24H), 1.23 (s, 3H, C22/23H), 1.06 (app-t, J=7.4, 3H, CO2CH2CH3), 1.02 (d, J=4.7, 1H, C18Hb), 0.80 (s, 3H, C22/23H). 13C NMR (150 MHz, CDCl3, 20 C.): delta 180.6 (C15), 169.5 (C13), 138.0 (SO2Ph-ipso-C), 134.5 (C9), 133.6 (SO2Ph-p-C), 129.9 (C4), 129.2 (SO2Ph-m-C), 126.7 (SO2Ph-o-C), 124.9 (C7), 124.7 (C2), 123.1 (C6), 122.3 (C3), 120.2 (C5), 113.5 (C8), 76.8 (C20), 67.7 (C12), 67.4 (C11), 61.1 (CO2CH2CH3), 50.3 (C19), 38.5 (C21), 38.2 (C17), 33.8 (C16), 28.1 (C24), 27.8 (C18), 27.1 (C22/23), 22.6 (C22/23), 13.7 (CO2CH2CH3). FTIR (thin film) cm-1: 3422 (br-m), 2926 (s), 1734 (s), 1649 (m), 1557 (w), 1448 (s), 1373 (s), 1273 (m), 1181 (s), 1126 (m), 1089 (m), 1022 (w), 978 (w), 920 (w), 751 (m). HRMS (ESI) (m/z): calc’d for C29H35N2O6S [M+H]+: 539.2210. found: 539.2198. TLC (50% ethyl acetate in hexanes), Rf: 0.49 (UV, CAM, KMnO4).

80360-20-9, As the paragraph descriping shows that 80360-20-9 is playing an increasingly important role.

Reference£º
Patent; Massachusetts Institute of Technology; The Board of Trustees of the University of Illinois; Movassaghi, Mohammad; Kim, Justin; Hergenrother, Paul J.; Morrison, Karen; Boyer, Nicolas; (186 pag.)US9353150; (2016); 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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1912-33-0,Methyl 2-(1H-indol-3-yl)acetate,as a common compound, the synthetic route is as follows.

(2) in a 500 ml round bottom flask methyl indole acetic acid is added in 9.46g (48mmol), ethylene glycol monomethyl ether (40 ml), 5 ml of hydrazine hydrate, 115 ¡ãC heating reflux reaction about 20 hours, thin layer chromatography (TLC) detecting raw material point dematerialised, stop the reaction, cooling to room temperature, adding water (50 ml), static separating white solid, filtering to get the crude product, using ethanol is recrystallized to get indole acetic acid hydrazide white solid 9.2 g.

1912-33-0, As the paragraph descriping shows that 1912-33-0 is playing an increasingly important role.

Reference£º
Patent; Kunming University of Science and Technology; Yunnan University; Xia, Xueshan; He, Yanping; Feng, Yue; Fan, Mengran; Gao, Fengpin; Zhang, Yufang; Li, Cong; (21 pag.)CN105732468; (2016); A;,
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

143612-79-7, 3-(4-Chlorobutyl)-1H-indole-5-carbonitrile is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Compound 3 (233 g, 1.0mol) and 6 (245 g, 1.0 mol) were dissolved in acetonitrile (3 L), and then, triethylamine (101 g, 1.0mol) and K2CO3 (138g,1.0mol) were added to the solution. The mixture was heated at reflux for 12 h. Subsequently, the reaction mixture was poured into cold water (3L). After filtration, the solid was dissolved in EtOAc, and then, HCl-EtOAc saturated solution was added to enable crystallization. Product 7 was obtained as a white solid. Yield 287 g (65%) with 99% HPLC purity after the mixture was filtered. m.p. 276.5-279.2C (Lit1 277-279C). 1H NMR (400MHz, DMSO-d6): delta 11.35 (s, 1H), 8.04 (d, J=18.3Hz, 2H), 7.74-6.88 (m, 8H), 3.69-3.15 (m, 8H), 2.74 (t, J= 7.2Hz, 2H), 2.37 (t, J =7.2Hz, 2H), 1.80-1.61 (m, 2H), 1.54 (d, J=6.8Hz, 2H). 13C NMR (100 MHz, DMSO-d6): delta 159.9, 148.8, 147.9, 138.6, 137.7, 127.8, 126.9, 124.7, 124.0, 123.3, 120.9, 117.8, 115.7, 112.4, 111.6, 109.5, 107.3, 100.0, 57.5, 52.8(2), 49.8(2), 27.7, 26.1, 24.1. HRMS (ESI): m/z [M+H]+ calculated for C26H27N5O2: 442.2238, found: 442.2240.

143612-79-7, As the paragraph descriping shows that 143612-79-7 is playing an increasingly important role.

Reference£º
Article; Hu, Fan; Su, Weike; Journal of Chemical Research; vol. 44; 3-4; (2020); p. 243 – 247;,
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