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En Route to 2-(Cyclobuten-1-yl)-3-(trifluoromethyl)-1H-indole. 2018

Martin Gazvoda, and Marko Krivec, and Zdenko Časar, and Janez Košmrlj
Faculty of Chemistry and Chemical Technology, University of Ljubljana , Vec̆na pot 113, SI-1000 Ljubljana, Slovenia.

A six-step synthetic route from 4-chloro-2-methylaniline to 5-chloro-2-(cyclobut-1-en-1-yl)-3-(trifluoromethyl)-1H-indole (1) has been reported. Compound 1a is a key impurity of reverse transcriptase inhibitor efavirenz, an important anti-HIV/AIDS drug. Synthetic challenges, dead ends, and detours are discussed.

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