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A practical synthesis of a COX-2-specific inhibitor
I W Davies1, J F Marcoux, E G Corley
1Department of Process Research, Merck & Co., Inc., P.O. Box 2000, Rahway, New Jersey 07065, USA. ian_davies1@merck.com
The Journal of Organic Chemistry
|December 12, 2000
Abstract:
A number of synthetic strategies to the Cox-2 specific inhibitor 1 have been described. These studies have led to the identification of a novel pyridine construction using annulation of ketone 2 using a vinamidinium species 29 and ammonia in 97% assay yield. Three approaches to the synthesis of ketone 2 are described that allow for its preparation in large quantities in >65% overall yield from methyl 6-methylnicotinate.