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

@article{Gazvoda2018EnRT,
  title={En Route to 2-(Cyclobuten-1-yl)-3-(trifluoromethyl)-1H-indole.},
  author={Martin Gazvoda and Marko Krivec and Zdenko {\vC}asar and Janez Ko{\vs}mrlj},
  journal={The Journal of organic chemistry},
  year={2018},
  volume={83 4},
  pages={
          2486-2493
        }
}
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. 
4 Citations
An entry to 2-(cyclobut-1-en-1-yl)-1H-indoles through a cyclobutenylation/deprotection cascade.
TLDR
Preliminary experimental and density functional theory calculations suggest that a Boc-group transfer is involved in the underlying mechanism of the synthesis of 2-(cyclobut-1-en- 1-yl)-1H-indoles. Expand
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