Issue 3, 2002
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Regioselective acylation of 1-hydroxypyrazoles via metalated intermediates

Niels Østergaard,ab   Niels Skjærbæk,a   Mikael Begtrupb  and  Per Vedsø*b  

* Corresponding authors

a ACADIA Pharmaceuticals A/S, Fabriksparken 58, DK-2600 Glostrup, Denmark
E-mail: ns@acadia-pharm.com
Fax: +45 43293030
Tel: +45 43293000

b The Royal Danish School of Pharmacy, Department of Medicinal Chemistry, Universitetsparken 2, DK-2100 Copenhagen Ø, Denmark
E-mail: pv@dfh.dk
Fax: +45 35306040
Tel: +45 35306487

Abstract

A range of C-4 and C-5 acylated 1-benzyloxypyrazoles (7a–e) and (4) have been prepared via Pd(0) catalysed cross-coupling between acid chlorides and 1-benzyloxy-4-(tributylstannyl)pyrazole (8) or 1-benzyloxypyrazol-5-ylzinc chloride. 3-Acylated 2-(4-methoxybenzyl)-2H-pyrazole 1-oxides (15a–f) were formed by reaction between the 3-magnesiated 2H-pyrazole 1-oxide (14) and acid chlorides. The benzyl group of 4 and 7a and the 4-methoxybenzyl (PMB) group of 15a were removed by treatment with conc. HCl or TFA in the presence of water, furnishing the corresponding C-acylated 1-hydroxypyrazoles.

Graphical abstract: Regioselective acylation of 1-hydroxypyrazoles via metalated intermediates

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Article information

DOI
https://doi.org/10.1039/B107850J
Article type
Paper
Submitted
05 Sep 2001
Accepted
26 Nov 2001
First published
03 Jan 2002

J. Chem. Soc., Perkin Trans. 1, 2002, 428-433

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Regioselective acylation of 1-hydroxypyrazoles via metalated intermediates

N. Østergaard, N. Skjærbæk, M. Begtrup and P. Vedsø, J. Chem. Soc., Perkin Trans. 1, 2002, 428 DOI: 10.1039/B107850J

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