Category: 165669-07-8

Organic Chemistry Frontiers | Cas: 165669-07-8 was involved in experiment

Application of 165669-07-8In addition to tryptophan, indigo, and indoleacetic acid, numerous compounds obtainable from plant or animal sources contain the indole molecular structure. The best-known group of these compounds is the indole alkaloids, members of which have been isolated from plants representing more than 30 families.

Application of 165669-07-8In 2020, Yuan, Yumeng;Pan, Guoshuai;Zhang, Xiaofeng;Huang, Qiufeng published 《One pot synthesis of pyrrolo[3,2,1-de]phenanthridines from 7-phenylindoles via tandem C-H olefination/aza-Michael addition》. 《Organic Chemistry Frontiers》published the findings. The article contains the following contents:

The one-pot C-H olefination/aza-Michael addition tandem process was developed for the synthesis of pyrrolo[3,2,1-de]phenanthridines from 7-phenylindoles and alkenes using a [Cp*RhCl2]2/AgOAc/Me4NOAc catalytic system. A relatively wide range of functional groups were tolerated, and a variety of pyrrolo[3,2,1-de]phenanthridines were obtained in good to excellent yields. And 7-Bromo-4-methyl-1H-indole (cas: 165669-07-8) was used in the research process.

Application of 165669-07-8In addition to tryptophan, indigo, and indoleacetic acid, numerous compounds obtainable from plant or animal sources contain the indole molecular structure. The best-known group of these compounds is the indole alkaloids, members of which have been isolated from plants representing more than 30 families.

Reference:
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

Bioorganic & Medicinal Chemistry Letters | Cas: 165669-07-8 was involved in experiment

Synthetic Route of C9H8BrNIn addition to tryptophan, indigo, and indoleacetic acid, numerous compounds obtainable from plant or animal sources contain the indole molecular structure. The best-known group of these compounds is the indole alkaloids, members of which have been isolated from plants representing more than 30 families.

Owa, Takashi;Okauchi, Tatsuo;Yoshimatsu, Kentaro;Sugi, Naoko Hata;Ozawa, Yoichi;Nagasu, Takeshi;Koyanagi, Nozomu;Okabe, Tadashi;Kitoh, Kyosuke;Yoshino, Hiroshi published 《A focused compound library of novel N-(7-indolyl)benzenesulfonamides for the discovery of potent cell cycle inhibitors》 in 2000. The article was appeared in 《Bioorganic & Medicinal Chemistry Letters》. They have made some progress in their research.Synthetic Route of C9H8BrN The article mentions the following:

A series of compounds containing an N-(7-indolyl)benzenesulfonamide pharmacophore, e.g. I, was synthesized and evaluated as a potential antitumor agent. Cell cycle anal. with P388 murine leukemia cells revealed that there were two different classes of potent cell cycle inhibitors; one disrupted mitosis and the other caused G1 accumulation. The structure-activity relationships of the substituent patterns on this pharmacophore template are described. And 7-Bromo-4-methyl-1H-indole (cas: 165669-07-8) was used in the research process.

Synthetic Route of C9H8BrNIn addition to tryptophan, indigo, and indoleacetic acid, numerous compounds obtainable from plant or animal sources contain the indole molecular structure. The best-known group of these compounds is the indole alkaloids, members of which have been isolated from plants representing more than 30 families.

Reference:
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

Cas: 165669-07-8 was involved in experiment | Journal of Organic Chemistry 2019

SDS of cas: 165669-07-8In addition to tryptophan, indigo, and indoleacetic acid, numerous compounds obtainable from plant or animal sources contain the indole molecular structure. The best-known group of these compounds is the indole alkaloids, members of which have been isolated from plants representing more than 30 families.

Yuan, Yumeng;Pan, Guoshuai;Zhang, Xiaofeng;Li, Buhong;Xiang, Shengchang;Huang, Qiufeng published 《Synthesis of seven-membered azepino[3,2,1-hi]indoles via rhodium-catalyzed regioselectively C-H activation/DBU-catalyzed intramolecualr amidation of 7-phenylindoles in one pot》. The research results were published in《Journal of Organic Chemistry》 in 2019.SDS of cas: 165669-07-8 The article conveys some information:

An unprecedented rhodium-catalyzed regioselectively C-H activation/DBU-catalyzed intramol. amidation cyclization of 7-arylindoles with diazomalonates is described that provides a straightforward route to seven-membered azepino[3,2,1-hi]indoles I (R1 = H, 12-Me, 11-F, etc.; R2 = 7-OMe, 7-tBu, 7-OH, etc.; R3 = CO2Me, CO2Et, CO2iPr) in good to excellent yields in one pot. A wide range of functional groups, including F, OMe, NPh2, SiMe3, Cl, CN, CHO, COMe, CO2Me, CF3, NO2 were all well tolerated.7-Bromo-4-methyl-1H-indole (cas: 165669-07-8) were involved in the experimental procedure.

SDS of cas: 165669-07-8In addition to tryptophan, indigo, and indoleacetic acid, numerous compounds obtainable from plant or animal sources contain the indole molecular structure. The best-known group of these compounds is the indole alkaloids, members of which have been isolated from plants representing more than 30 families.

Reference:
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

Cas: 165669-07-8 | Dobbs, Adrianpublished an article in 2001

Application In Synthesis of 7-Bromo-4-methyl-1H-indoleIn addition to tryptophan, indigo, and indoleacetic acid, numerous compounds obtainable from plant or animal sources contain the indole molecular structure. The best-known group of these compounds is the indole alkaloids, members of which have been isolated from plants representing more than 30 families.

Dobbs, Adrian published 《Total Synthesis of Indoles from Tricholoma Species via Bartoli/Heteroaryl Radical Methodologies》 in 2001. The article was appeared in 《Journal of Organic Chemistry》. They have made some progress in their research.Application In Synthesis of 7-Bromo-4-methyl-1H-indole The article mentions the following:

The Bartoli reaction of o-bromonitrobenzene with simple vinyl Grignard reagents was performed yielding a range of complex 7-bromo-substituted indoles followed by radical reduction using Bu3Sn/AIBN in toluene to give 7-unsubstituted indoles in near quant. yields. The total synthesis of three indole alkaloids I (R = H, OH, OMe) was then achieved via this Bartoli synthesis/heteroaryl radical reduction approach. To complete the study, the researchers used 7-Bromo-4-methyl-1H-indole (cas: 165669-07-8) .

Application In Synthesis of 7-Bromo-4-methyl-1H-indoleIn addition to tryptophan, indigo, and indoleacetic acid, numerous compounds obtainable from plant or animal sources contain the indole molecular structure. The best-known group of these compounds is the indole alkaloids, members of which have been isolated from plants representing more than 30 families.

Reference:
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

Cas: 165669-07-8 | Pan, Guoshuai et al. made new progress in 2021

Application of 165669-07-8In addition to tryptophan, indigo, and indoleacetic acid, numerous compounds obtainable from plant or animal sources contain the indole molecular structure. The best-known group of these compounds is the indole alkaloids, members of which have been isolated from plants representing more than 30 families.

Pan, Guoshuai;Lu, Leipeng;Zhuang, Weihui;Huang, Qiufeng published 《Synthesis of Indole-Fused Six-, Seven-, or Eight-Membered N,O-Heterocycles via Rhodium-Catalyzed NH-Indole-Directed C-H Acetoxylation/Hydrolysis/Annulation》 in 2021. The article was appeared in 《Journal of Organic Chemistry》. They have made some progress in their research.Application of 165669-07-8 The article mentions the following:

The facile synthesis of indole-fused six-, seven-, or eight-membered N,O-heterocycles I/II (R = H, Cl, Br) and III/IV and V through rhodium-catalyzed C-H acetoxylation/hydrolysis/annulation was reported. The notable features of this method include C-H acetoxylation using NH-indole as the intrinsic directing group, high functional group compatibility, and construction of indole-fused medium-sized rings. To complete the study, the researchers used 7-Bromo-4-methyl-1H-indole (cas: 165669-07-8) .

Application of 165669-07-8In addition to tryptophan, indigo, and indoleacetic acid, numerous compounds obtainable from plant or animal sources contain the indole molecular structure. The best-known group of these compounds is the indole alkaloids, members of which have been isolated from plants representing more than 30 families.

Reference:
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

New learning discoveries about 165669-07-8

The synthetic route of 165669-07-8 has been constantly updated, and we look forward to future research findings.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.165669-07-8,7-Bromo-4-methyl-1H-indole,as a common compound, the synthetic route is as follows.

To a mixture of potassium hydride (4.47 g, 34.27 mmol, 30 wt %) suspended in anhydrous tetrahydrofuran (80 mL) was added 7-bromo-4-methyl-1H-indole (6.00 g, 28.56 mmol) dissolved in tetrahydrofuran (30 mL) at 0 C. After 15 minutes, the mixture was cooled to -70 C. and t-BuLi (1.3 M, 54.9 mL) was added dropwise, keeping the temperature below -65 C. After further 15 minutes, carbon dioxide gas (15 psi pressure) was bubbled into the reaction and the reaction was slowly warmed to rt over 30 minutes. On completion, the reaction mixture was quenched with ice water (120 mL), and washed with ethyl acetate (3¡Á60 mL). The aqueous phase was collected and acidified with 1 N hydrochloride acid solution until the pH<7. Then, the mixture was extracted with ethyl acetate (3¡Á60 mL). The organic phase was collected, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give the crude product as a brown solid. The crude product was triturated with petroleum ether:dichloromethane (10:1, 100 mL) to give the product (3.50 g, 69% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) delta 12.82 (br s, 1H), 11.02 (br s, 1H), 7.67 (d, J=7.6 Hz, 1H), 7.35 (t, J=2.8 Hz, 1H), 6.92 (d, J=7.6 Hz, 1H), 6.56 (dd, J=2.0, 3.2 Hz, 1H), 2.54 (s, 3H)., 165669-07-8

The synthetic route of 165669-07-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Kymera Therapeutics, Inc.; Mainolfi, Nello; Ji, Nan; Kluge, Arthur F.; Weiss, Matthew M.; Zhang, Yi; (1443 pag.)US2019/192668; (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

Simple exploration of 165669-07-8

165669-07-8, As the paragraph descriping shows that 165669-07-8 is playing an increasingly important role.

165669-07-8, 7-Bromo-4-methyl-1H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

(4-methyl-1 H-indol-7-yl)(phenyl)methanamine – To a solution of 1 -bromo-4-methyl-2-nitrobenzene (2.0 g, 9.26 mmol) in THF was added vinyl magnesium bromide 1 M in THF (27.8 ml_, 27.77 mmol) at – 50C. The reaction was finished after 1 h30. The reaction was quenched with sat. NH4CI. The aqueous layer was extracted with a non-water miscible organic solvent. The combined organic layers were dried over MgS04, filtered and the solution was concentrated to dryness. The crude material was purified on silica gel column chromatography usinf hexanes/EtOAc (9:1 ) as eluent. A solution of the freshly synthesized 7-bromo-4-methyl-1 H-indole (1 .1 g, 5.24 mmol), zinc cyanide (860 mg, 7.32 mmol) and Pd(PPh3)4 (0.03 eq.) in DMF Ex.97 was heated under microwave irradiation at 170C for 1 h. After cooling, water was added to quench the reaction. The aqueous layer was extracted with a non-water miscible organic solvent. The combined organic layers were dried over MgS04, filtered and the solution was concentrated under reduced pressure. The crude material was purified on silica gel column chromatography using hexanes/EtOAc (12:1 to 4:1 ) as eluent. The titled compound was then obtained following the modified procedure described in WO2006035157 (Protocol A) – Yield: 2% ; appearance: pale brown solid ; 1 H NMR, d (ppm) (Methanol d4) : 2.49 (s, 3H); 5.51 (s, 1 H); 6.47 (d, 1 H, J=3.2Hz); 6.81 (dd, 1 H, J=0.6Hz , J=7.3Hz); 7.01 (d, 1 H, J=7.3Hz); 7.17-7.22 (m, 2H); 7.25-7.31 (m, 2H); 7.39- 7.43 (m, 2H)

165669-07-8, As the paragraph descriping shows that 165669-07-8 is playing an increasingly important role.

Reference£º
Patent; GENFIT; DELHOMEL, Jean-Francois; WALCZAK, Robert; MAJD, Zouher; PIHAN, Emilie; BONNET, Pascal; PERSPICACE, Enrico; (198 pag.)WO2016/102633; (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