| Autor: |
Chen K; Chemical Development, Bristol-Myers Squibb , 1 Squibb Drive, New Brunswick, New Jersey 08903, United States., Risatti C, Bultman M, Soumeillant M, Simpson J, Zheng B, Fanfair D, Mahoney M, Mudryk B, Fox RJ, Hsaio Y, Murugesan S, Conlon DA, Buono FG, Eastgate MD |
| Jazyk: |
angličtina |
| Zdroj: |
The Journal of organic chemistry [J Org Chem] 2014 Sep 19; Vol. 79 (18), pp. 8757-67. Date of Electronic Publication: 2014 Sep 05. |
| DOI: |
10.1021/jo5016008 |
| Abstrakt: |
The development of a short and efficient synthesis of a complex 6-azaindole, BMS-663068, is described. Construction of the 6-azaindole core is quickly accomplished starting from a simple pyrrole, via a regioselective Friedel-Crafts acylation, Pictet-Spengler cyclization, and a radical-mediated aromatization. The synthesis leverages an unusual heterocyclic N-oxide α-bromination to functionalize a critical C-H bond, enabling a highly regioselective copper-mediated Ullmann-Goldberg-Buchwald coupling to install a challenging triazole substituent. This strategy resulted in an efficient 11 step linear synthesis of this complex clinical candidate. |
| Databáze: |
MEDLINE |
| Externí odkaz: |
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