Synthesis 2014; 46(07): 899-908
DOI: 10.1055/s-0033-1340679
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of 2-(4-Isopropylthiazol-2-yl)-7-methoxy-8-methylquinolin-4-ol; A Quinoline Building Block for Simeprevir Synthesis

Stanislav Rádl*
a  Zentiva – A Sanofi Company, U kabelovny 130, 102 37 Prague, Czech Republic   Fax: +420(2)67243741   Email: stanislav.radl@zentiva.cz
b  Institute of Chemical Technology, Technická 5, 166 28 Prague, Czech Republic
,
Hana Rezková
b  Institute of Chemical Technology, Technická 5, 166 28 Prague, Czech Republic
,
Iva Obadalová
a  Zentiva – A Sanofi Company, U kabelovny 130, 102 37 Prague, Czech Republic   Fax: +420(2)67243741   Email: stanislav.radl@zentiva.cz
,
Jan Srbek
a  Zentiva – A Sanofi Company, U kabelovny 130, 102 37 Prague, Czech Republic   Fax: +420(2)67243741   Email: stanislav.radl@zentiva.cz
,
Jiří Břicháč
a  Zentiva – A Sanofi Company, U kabelovny 130, 102 37 Prague, Czech Republic   Fax: +420(2)67243741   Email: stanislav.radl@zentiva.cz
,
Tomáš Pekárek
a  Zentiva – A Sanofi Company, U kabelovny 130, 102 37 Prague, Czech Republic   Fax: +420(2)67243741   Email: stanislav.radl@zentiva.cz
› Author Affiliations
Further Information

Publication History

Received: 07 November 2013

Accepted after revision: 08 January 2014

Publication Date:
30 January 2014 (eFirst)

Dedicated to my friend and admirable human being Dr. Alfred Bader on the occasion of his 90th birthday (S.R.).

Abstract

Two synthetic approaches to the achiral quinoline fragment of simeprevir are described. Both approaches are based on the synthesis of methyl 4-hydroxy-7-methoxy-8-methylquinoline-2-carboxylate, protection of its 4-hydroxyl group, and construction of the thiazole ring from the ester group at the 2-position. The last step is acid deprotection of the 4-hydroxyl protecting group.

Supporting Information

 
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