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Synfacts 2010(1): 0115-0115  
DOI: 10.1055/s-0029-1218442
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Parallel Solid-Phase Synthesis of Iodinated Analogues of Rimonabant

Contributor(s): Yasuhiro Uozumi, Yoichi M. A. Yamada, Maki Minakawa
A. C. Spivey*, C.-C. Tseng, T. C. Jones, A. D. Kohler, G. J. Ellames
Imperial College, London and Sanofi-Aventis, Alnwick, UK
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Publication History

Publication Date:
21 December 2009 (online)

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Significance

A novel method for the parallel ­solid-phase synthesis of iodinated analogues of the CB1 receptor inverse agonist rimonabant was described. HypoGel-bound 1,5-diarylpyrazole tert-butyl ester 6 was prepared by employing ­HypoGel-bound gelmanium bromide 4 via transmetalation. Parallel amidation of 6 with hydrazines and amines gave HypoGel-bound 1,5-arylpyrazolyl hydrazides/amides 7a-e. Cleavage of the Ge linker with concomitant ipso-iodination afforded iodinated rimonabant analogues 1a-e (5 examples, 42-63% yield, 1-6 h).