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An alternative synthesis of Vandetanib (CaprelsaTM) via a microwave accelerated Dimroth rearrangement
Brocklesby, K.L. Waby, Jennifer S. Cawthorne, C. Smith, G.
Brocklesby, K.L.
Waby, Jennifer S.
Cawthorne, C.
Smith, G.
Publication Date
2017-04-12
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©2017 The Authors. Published by Elsevier Ltd. This is an open access article under the CC BY license (http://
creativecommons.org/licenses/by/4.0/).
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2017-02-27
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Abstract
Vandetanib is an orally available tyrosine kinase inhibitor used in the treatment of cancer. The current
synthesis proceeds via an unstable 4-chloroquinazoline, using harsh reagents, in addition to requiring
sequential protection and deprotection steps. In the present work, use of the Dimroth rearrangement
in the key quinazoline forming step enabled the synthesis of Vandetanib in nine steps (compared to
the previously reported 12–14).
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Citation
Brocklesby KL, Waby JS, Cawthorne C et al (2017) An alternative synthesis of Vandetanib (CaprelsaTM) via a microwave accelerated Dimroth rearrangement. Tetrahedron Letters. 58(15): 1467-1469.
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