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Synfacts 2011(12): 1266-1266  
DOI: 10.1055/s-0031-1289317
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of MK-3281

Contributor(s): Philip Kocienski
J. P. Scott*, M. Alam, N. Bremeyer, A. Goodyear, T. Lam, R. D. Wilson, G. Zhou
Merck Sharp & Dohme Research Laboratories, Hoddesdon, UK; Merck and Co. Inc., Rahway, USA
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Publication History

Publication Date:
18 November 2011 (online)

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Significance

The synthesis of hepatitis C RNA polymerase NS5B inhibitor MK-3281 delivered 3 kg of the API in 32% overall yield and >99% optical purity. A key step is the intramolecular N-alkyl­ation of the indole C to form the eight-membered benzoxazocine ring in D.