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Synlett 2001; 2001(12): 1917-1920
DOI: 10.1055/s-2001-18758
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Combinatorial Synthesis of 5-Aryl-[1,2,4]-triazolo-[1,5-a]-pyridine Derivatives as Potential Inhibitors of the Adenosine 2A Receptor

Matthias Nettekoven*
  • *F. Hoffmann-La Roche Ltd., Pharmaceutical Research Preclinical Division, Lead Generation, Discovery Chemistry, CH-4070 Basel, Switzerland; Fax: + 41(61)6886459; E-mail: matthias.nettekoven@roche.com
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Publication Date:
04 December 2001 (online)

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A novel and efficient 4-step synthesis of 2,4-diamino-4-bromo-pyridine 4 in 56% overall yield by a double Curtius rearrangement as a key step is reported. N-amination of 2,4-diamino-4-bromo-pyridine 4 with O-mesitylenesulfonylhydroxylamine 10 and subsequent reaction with aldehydes yielded, upon oxidative ring-closure, 5-bromo-triazolopyridines 2a-2f. Thereafter, from a combinatorial parallel Suzuki cross-coupling reaction 260 previously non-described 5-aryl-[1,2,4]-triazolo-[1,5-a]-pyridines 1 were obtained in acceptable overall yield.

Adenosine 2A - double-Curtius rearrangement - N-amination - Suzuki cross-coupling reaction - 7-amino-triazolopyridine derivatives