Synthesis of differentially protected azatryptophan analogs via Pd2(dba)3/XPhos catalyzed Negishi coupling of N-Ts azaindole halides with zinc derivative from Fmoc-protected tert-butyl (R)-2-amino-3-iodopropanoate was written by Nimje, Roshan Y.;Vytla, Devaiah;Kuppusamy, Prakasam;Velayuthaperumal, Rajeswari;Jarugu, Lokesh Babu;Reddy, China Anki;Chikkananjaiah, Nanjundaswamy Kanikahalli;Rampulla, Richard A.;Cavallaro, Cullen L.;Li, Jianqing;Mathur, Arvind;Gupta, Anuradha;Roy, Amrita. And the article was included in Journal of Organic Chemistry in 2020.Application In Synthesis of 3-Bromo-4-chloro-7-azaindole This article mentions the following:
Unnatural amino acids play an important role in peptide based drug discovery. Herein, we report a class of differentially protected azatryptophan derivatives synthesized from N-tosyl-3-haloazaindoles (I) (Pg = protective groups: Ts (tosyl), Fmoc (9-fluorenylmethoxycarbonyl), and tert-Bu) and Fmoc-protected tert-Bu iodoalanine (II) (Fmoc = 9-fluorenylmethoxycarbonyl) via a Negishi coupling. Through ligand screening, Pd2(dba)3/XPhos was found to be a superior catalyst for the coupling of 1 with the zinc derivative of 2 to give tert-Bu (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)propanoate derivatives (III) (Pg = protective groups: Ts, Fmoc, and tert-Bu; Fmoc = 9-fluorenylmethoxycarbonyl) in 69-91% isolated yields. In addition, we have demonstrated that the protecting groups, namely, Ts, Fmoc, and tert-Bu, can be easily removed selectively. In the experiment, the researchers used many compounds, for example, 3-Bromo-4-chloro-7-azaindole (cas: 1000340-39-5Application In Synthesis of 3-Bromo-4-chloro-7-azaindole).
3-Bromo-4-chloro-7-azaindole (cas: 1000340-39-5) belongs to indole derivatives. Indole is an important structural motif of various drugs, therapeutic leads besides its prevalence in numerous natural products, agrochemicals, perfumery, and dyes. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Application In Synthesis of 3-Bromo-4-chloro-7-azaindole
Referemce:
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