An improved synthesis of etravirine

Joshi, Shashikant ; Maikap, Golak C. ; Titirmare, Shyam ; Chaudhari, Ashok ; Gurjar, Mukund K. (2010) An improved synthesis of etravirine Organic Process Research & Development, 14 (3). pp. 657-660. ISSN 1083-6160

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Etravirine (1) is a novel diarylpyrimidine non-nucleoside reverse transcriptase inhibitor and has recently been approved by the U.S. Federal Drug Administsration for the treatment of AIDS. Its reported synthesis is fraught with many difficulties, the foremost being the poor yield and long reaction time required at the aminolysis stage. We attributed this problem to the presence of a bromide group adjacent to the reaction site of the advance intermediate (6). In order to circumvent this issue, we proposed to defer the installation of the bromide group at a later stage, preferably after aminolysis. Indeed, this protocol has worked well. However, in the process of installation of diarylether and diarylamine functionalities at appropriate positions, we had to reverse the sequence of displacement reactions of the dichloride intermediate (9) with 3,5-dimethyl-4-hydroxybenzonitrile (5) and 4-aminobenzonitrile (3). The classical bromination led to the completion of etravirine synthesis.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society.
ID Code:11391
Deposited On:09 Nov 2010 05:37
Last Modified:02 Jun 2011 09:36

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