Indole Building Blocks

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1202-04-6,Methyl 1H-indole-2-carboxylate,as a common compound, the synthetic route is as follows.

Add 0.063 g (0.5 mmol) of 2-indolecarboxylic acid methyl ester to the reaction flask.Diphenylphosphine oxide 0.202 g (1 mmol),0.013 g (0.05 mmol) of silver carbonate,4 A molecular sieve 0.2 g,Magnesium nitrate 0.148 g (1 mmol) and 30 ml ethanol,60 C reaction;TLC tracks the reaction until it is completely over;The crude product obtained after the completion of the reaction was separated by column chromatography ( petroleum ether: ethyl acetate = 4:1).The target product was obtained (yield 95%), 1202-04-6

As the paragraph descriping shows that 1202-04-6 is playing an increasingly important role.

Reference£º
Patent; Suzhou University Zhangjiagang Industry Technology Institute; Soochow University (Suzhou); Zou Jianping; Xue Jianfei; Zhou Shaofang; Zhang Peizhi; (12 pag.)CN104926868; (2018); B;,
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

387-44-0, 7-Fluoroindole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: Quinoline moiety – General Procedure Q In microwave vessel, quinoline (2.oeq) and indole (i.oeq) were mixed together and the system was sealed and placed under nitrogen, after a purge with vacuum/N2 (3 times). Then, HC1 solution 4 M in 1,4-dioxane (i.2eq) was added with the needle immersed in the mixture (exothermic reaction). The reaction mixture was heated with microwave during 2 h at 160 C. The reaction mixture was taken up with a minimum of MeOH and when the residue was dissolved, it was transferred in mixture of AcOEt and saturated NaHC03 solution. The resulting solution was extracted and the aqueous phase was washed with AcOEt (x2). The organic layers were combined, washed with o.oi M critic acid solution, saturated NaHC03 solution, dried over Na2S04 and concentrated to dryness under reduced pressure. Finally, the crude was purified by automated combi-flash to afford the good compound., 387-44-0

387-44-0 7-Fluoroindole 2774504, aindole-building-block compound, is more and more widely used in various fields.

Reference£º
Patent; THE UNIVERSITY OF BRITISH COLUMBIA; SIMON FRASER UNIVERSITY; RENNIE, Paul; TCHERKASSOV, Artem; YOUNG, Robert, N.; ANDRE, Christophe, M.; WO2015/154169; (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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.18372-22-0,Methyl 2-(1H-indol-3-yl)-2-oxoacetate,as a common compound, the synthetic route is as follows.

To a suspension of compound 12 (1.17 g, 5.7 mmol) and compound 6 (586.5 mg, 2.9 mmol) in THF (50 mL) was added 1.0 M KOBut in THF (11.5 mL, 11.5 mmol) under nitrogen atmosphere. After stirring at ambient temperature for 5 h, thereaction mixture was quenched with 1 N HCl (50 mL) and extracted with EtOAc. The combined organic layer was washed with brine, dried over Na2SO4, and filtered. The solvent was removed in vacuo, and the crude product waspurified by column chromatography with (2:1 hexanes/acetone) to give 13 (726.0 mg, 71%) as an orange solid: mp 254 – 256 C; 1H NMR (DMSO-d6) delta 12.02 (s, 1H), 11.19 (s, 1H), 8.04 (d, J = 3.0 Hz, 1H), 7.73 (d, J = 2.0 Hz, 1H), 7.49 (dd, J = 2.0, 8.5 Hz, 1H), 7.43 (dd, J = 3.0, 8.5 Hz, 2H), 7.09-7.06 (m, 1H), 6.76-6.73 (m, 1H), 6.40(d, J = 8.0 Hz, 1H); HRMS (EI, m/z): calcd for C18H10N2O2Cl2 ([M]+) 356.0114, found 356.0126.

18372-22-0, As the paragraph descriping shows that 18372-22-0 is playing an increasingly important role.

Reference£º
Article; Wang, Min; Gao, Mingzhang; Miller, Kathy D.; Sledge, George W.; Hutchins, Gary D.; Zheng, Qi-Huang; Bioorganic and Medicinal Chemistry Letters; vol. 21; 1; (2011); p. 245 – 249;,
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

1953-54-4, 5-Hydroxyindole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A solution of 5 g (37.55 mmol) of 5-hydroxy-indole, 6.13 g (39.4 mmol) of tert-butyldimethylsilyl chloride and 5.37 g (68.1 mmol) of imidazole in 50 ml DMF was stirred for 20 h at RT. The reaction mixture was taken up in ether, washed with 1N HCl and water and the ether solution was then concentrated under reduced pressure, to give 9.4 g (quant.) of clean 5-(tert-butyl-dimethyl-silanyloxy)-1H-indole. MS: 248.1 (M+H)+.

1953-54-4, 1953-54-4 5-Hydroxyindole 16054, aindole-building-block compound, is more and more widely used in various fields.

Reference£º
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.52488-36-5,4-Bromo-1H-indole,as a common compound, the synthetic route is as follows.

Under a nitrogen atmosphere, cuprous iodide (3.0 mol%, 0.7 mg), sodium iodide (1.0 equiv., 18.7 mg) and magnets were added to a previously baked 10 mL glass pressure tube. Dioxane (0.2 mL), 4-bromoindole (0.125 mmol, 1.0 equiv., 24.5 mg) and N,N’-dimethylethylenediamine (10.0 mol%, 1.1 mg) were then added. After the addition, the glass pressure tube was placed in a metal module that had been preheated to 100 C. and stirred for 10 hours. Cooled to room temperature, cuprous oxide was added under a nitrogen atmosphere (20mol%, 3.6mg), nine carbonyl iron (3mol%, 1.4mg), N- methylpyrrolidinone (0.5mL) and phenyl silane (3.0equiv., 40.6 Mg). The tube was purged of air and charged with carbon dioxide (5.0 equiv., 15 mL) and ammonia gas (5.0 equiv., 15 mL). After the addition was completed, the reactor was placed in a metal module preheated to 160C and stirred for 10 hours. After the reaction was completed, the reaction system was cooled to room temperature and pressure was slowly released. Use of dodecane as an internal standard through gas chromatography The working curve determines that the yield is 84%., 52488-36-5

52488-36-5 4-Bromo-1H-indole 676494, aindole-building-block compound, is more and more widely used in various fields.

Reference£º
Patent; Chinese Academy Of Sciences Lanzhou Chemical Physics Institute Suzhou Institute; Li Yuehui; Wang Hua; Dong Yanan; Ke Lisitian¡¤shanduofu; (20 pag.)CN108017557; (2018); 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

1912-33-0, Methyl 2-(1H-indol-3-yl)acetate is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Methyl indole-3-acetate (2.00 g, 10.57 mmol) was dissolved in dichloromethane (30 ml). To this solution, tetrabutylammonium iodide (TBAI, 30.0 mg, 0.081 mmol) and a 30% aqueous sodium hydroxide solution (24 ml) were added, and the mixture was cooled to 0 C. To the reaction solution, methyl formate chloride (1.96 g, 20.73 mmol) was added, and the mixture was stirred at 0 C. for 2 hours. After the reaction was confirmed by TLC to be complete, the reaction was terminated by the addition of 6 N hydrochloric acid. Water (50 ml) was added thereto, followed by extraction with chloroform (50 ml) three times. The organic layer was washed twice with saturated saline and dehydrated over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and then, the residue was purified using silica gel column chromatography (hexane:ethyl acetate=8:2) to obtain methyl N-methoxycarbonylindole-3-acetate (2.26 g, yield: 87%): 1H NMR (400 MHz, CDCl3): delta 8.18 (d, J=7.0 Hz, 1H), 7.59 (s, 1H), 7.53 (d, J=7.7 Hz, 1H), 7.35 (t, J=7.5 Hz, 1H), 7.27 (t, J=7.4 Hz, 1H), 4.00 (s, 3H), 3.72 (s, 3H), 3.71 (s, 2H); 13C NMR (100 MHz, CDCl3): delta 171.1, 151.1, 135.2, 129.9, 124.6, 123.8, 122.8, 118.9, 115.0, 113.8, 53.5, 51.9, 30.6; IR (neat): 1746, 1455, 1382, 1258, 1164, 1089, 1018 cm-1; EI-MS: m/z 247 [M]+., 1912-33-0

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

Reference£º
Patent; Tohoku University; Kake Educational Institution; Abe, Takaaki; Katori, Yukio; Honkura, Yohei; Nanto, Fumika; Hayashi, Kenichiro; (77 pag.)US2019/224165; (2019); 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.5457-28-3,1H-Indole-3-carbonitrile,as a common compound, the synthetic route is as follows.

To a 1 L four-neck flask were added dioxane (200 mL), THF (100 mL) and 3- cyanoindole (30 g, 211 mmol). The solution was cooled to 0 oC and LiAlH4 (30 g, 780 mmol) was added portion-wise. After stirring at 0 oC for 10 minutes, the mixture was heated to reflux for 0.5 h until TLC showed completion. The mixture was carefully quenched with water (300 mL) at 0 oC, filtered, and the filtrate was separated. The aqueous layer was extracted with EA (500 mL x 2). The combined organic layers were dried over sodium sulfate, concentrated and washed with PE/EA to give 3-aminomethylindole (21 g, 70percent) as a brick red solid. (2137) 1H NMR (300 MHz, DMSO-d6) 10.80 (br, 1 H), 7.59 (d, J = 7.5 Hz, 1 H), 7.34 (d, J = 8.1 Hz, 1 H), 7.20 (s, 1 H), 7.09- 7.04 (m, 1 H), 6.99- 6.94 (m, 1 H), 3.87 (s, 2 H)., 5457-28-3

5457-28-3 1H-Indole-3-carbonitrile 230282, aindole-building-block compound, is more and more widely used in various fields.

Reference£º
Patent; CS PHARMASCIENCES, INC.; SONG, Yuntao; BRDIGES, Alexander, James; (524 pag.)WO2017/120429; (2017); 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

16732-70-0, Ethyl 5-bromo-1H-indole-2-carboxylate is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A mixture of 5-Bromo-lH-indole-2-carboxylic acid ethyl ester (50 mg, 0.186 mmol) and l-fluoro-2,4,6-trimethylpyridinium triflate (204 mg, 0.60 mmol) are dissolved in tetrachloroethane (1 ml) and heated to 100 0C for 30 minutes. The reaction is diluted with ethyl acetate washed with water and brine. The organic layer is dried (sodium sulfate), filtered and concentrated in vacuo to give an oil that is purified by reverse phase EtaPLC to give the title compound as a white solid 27 mg, 50%, LC/MS ESI m/z (M+Eta)+ = 286.31.

16732-70-0, As the paragraph descriping shows that 16732-70-0 is playing an increasingly important role.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ABEYWARDANE, Asitha; FARMER, Bennett; FARROW, Neil Alexander; GAO, Donghong A.; HEIM-RIETHER, Alexander; KEENAN, Lana Louise Smith; MUGGE, Ingo Andreas; TAYLOR, Steven John; XIONG, Zhaoming; YU, Yang; ZHANG, Qiang; WO2010/45188; (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

348640-06-2, 4-Bromo-7-azaindole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine A mixture of 4-bromo-1H-pyrrolo[2,3-b]pyridine (10.0 g, 51.0 mmol), Pin2B2 (15.5 g, 61.0 mmol), PdCl2(dppf) (2.0 g, 2.5 mmol) and KOAc (10.0 g, 102 mmol) in 1,4-dioxane (200 mL) was degassed with Ar for 5 minutes. The reaction mixture was heated to 80 C. and stirred for 16 h. The mixture was cooled to RT, filtered through CELITE and concentrated under reduced pressure. The residue was purified via silica gel chromatography (0-25% EtOAc in hexanes) to afford the title compound (3.8 g, 31% yield) as a white solid. MS (ES+) C13H17BN2O2 requires: 244, found: 245 [M+H]+., 348640-06-2

The synthetic route of 348640-06-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Board of Regents, The University of Texas System; DI FRANCESCO, Maria Emilia; JONES, Philip; CARROLL, Christopher Lawrence; CROSS, Jason Bryant; RAMASWAMY, Suyambu Kesava Vijayan; JOHNSON, Michael Garrett; LIVELY, Sarah; LAPOINTE, David; US2019/16713; (2019); 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.858515-65-8,4-Methyl-1H-indole-3-carboxylic acid,as a common compound, the synthetic route is as follows.

858515-65-8, A procedure for converting quinuclidin-4-ylmethyl 4-methyl-l//-indole-3-carboxylate phosphate salt (93% assay purity; mix of polymorphs) to quinuclidin-4-ylmethyl 4-methyl-lH- indole-3-carboxylate phosphate salt (polymorphic Form A) is shown in Scheme 1. step 1: A solution of 4-methyl-lH-indole-3-carboxylic acid (1.88 kg) in DMF (0.54 kg) I was added to DCM (63 kg) in a reactor. The system was vacuumed and refilled with N2 for three cycles. The solution was heated to 25-35 C (internal temperature). Oxalyl chloride (2.7 kg) Lambda was added drop-wise over 2 hr while maintaining the temperature at 25-35 C under nitrogen. The mixture was stirred for 4 hrs at 25-35 C under nitrogen. The reaction mixture was concentrated under vacuum (0.08 Mpa) at 30-35 C to about 15-20 L and evaporated at 35 ¡À 5 C using a rotary evaporator to remove DCM and oxalyl chloride until an obvious distillate was observed. The reaction mixture was charged with DCM (15.0 kg) and evaporated to dryness, and this charge-evaporate procedure was repeated for two cycles. Fifteen kilograms of DCM was charged to the mixture and stirred to obtain a clear solution, and an additional 15 kg of DCM was charged to the mixture in the rotary evaporator. The solution in the rotary evaporator was transferred to a dropping tank under nitrogen. Quinuclidin-4-ylmethanol N-borane complex (1.5 kg) and Et3N (1.65 kg) were added to a reactor containing DCM (15.0 kg). The mixture was cooled to 0-5 C (internal temperature), and the solution from the dropping tank in the previous step was added over 2 hrs under nitrogen at 0-5 C. The mixture was heated to 15-25 C with stirring and was stirred at 15- 25 C for 16 hrs under nitrogen. Saturated NH4CI solution (20.3 kg) was added dropwise to quench this reaction at 15-25 C. The mixture was stirred for 30 min and settled aside for 15 min. The organic layer was separated and washed with brine (40.8 kg) and dried with anhydrous Na2SC4 (3.0 kg). The solid was filtered, and the cake was washed with DCM (3.0 kg).

The synthetic route of 858515-65-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ALPHARMAGEN, LLC; NG, John, Sau-Hoi; NG, Raymond; (86 pag.)WO2017/120532; (2017); 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