A practical synthesis of a COX-2-specific inhibitor

Authors
Davies, IW Marcoux, JF Corley, EG Journet, M Cai, DW Palucki, M Wu, J Larsen, RD Rossen, K Pye, PJ DiMichele, L Dormer, P Reider, PJ
Citation
Iw. Davies et al., A practical synthesis of a COX-2-specific inhibitor, J ORG CHEM, 65(25), 2000, pp. 8415-8420
Citations number
32
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
65
Issue
25
Year of publication
2000
Pages
8415 - 8420
Database
ISI
SICI code
0022-3263(200012)65:25<8415:APSOAC>2.0.ZU;2-3
Abstract
A number of synthetic strategies to the Cox-2 specific inhibitor 1 have bee n described. These studies have led to the identification of a novel pyridi ne construction using annulation of ketone 2 using a vinamidinium species 2 9 and ammonia in 97% assay yield. Three approaches to the synthesis of keto ne 2 are described that allow for its preparation in large quantities in >6 5% overall yield from methyl 6-methylnicotinate.