RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000131.xml
Synfacts 2014; 10(12): 1239
DOI: 10.1055/s-0034-1379407
DOI: 10.1055/s-0034-1379407
Synthesis of Natural Products and Potential Drugs
Synthesis of BMS-663068
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
18. November 2014 (online)
Key words
BMS-663068 - HIV attachment inhibitors - 6-azaindoles - Ullmann–Goldberg–Buchwald coupling - brominationSignificance
Attachment inhibitor BMS-663068 is currently in clinical development for the treatment of HIV infection. Key steps in the synthesis depicted are (1) a radical-mediated redox-aromatization to generate the 6-azaindole (B → C) and (2) the regioselective bromination of an N-oxide using PyBroP (D → E).
#
Comment
High regioselectivity was observed in the copper(I)-mediated Ullmann–Goldberg–Buchwald coupling (H → K) using the diamine ligand J (N1/N2 = 22:1), whereas a thermal SNAr reaction gave N1/N2 = 1:1. Alternative conditions for the bromination of the N-oxide D led mainly to deoxygenation.
#
#