title: A practical synthesis of a COX-2-specific inhibitor.
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.
authors: Department of Process Research, Merck & Co., Inc., P.O. Box 2000, Rahway, New Jersey 07065, USA. ian_davies1@merck.com
authors: I W
authors: IW
authors: Davies
authors: J F
authors: JF
authors: Marcoux
authors: E G
authors: EG
authors: Corley
authors: M
authors: M
authors: Journet
authors: D W
authors: DW
authors: Cai
authors: M
authors: M
authors: Palucki
authors: J
authors: J
authors: Wu
authors: R D
authors: RD
authors: Larsen
authors: K
authors: K
authors: Rossen
authors: P J
authors: PJ
authors: Pye
authors: L
authors: L
authors: DiMichele
authors: P
authors: P
authors: Dormer
authors: P J
authors: PJ
authors: Reider
mesh_terms: D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis*; D002851:Chromatography, High Pressure Liquid; D051546:Cyclooxygenase 2; D052246:Cyclooxygenase 2 Inhibitors; D016861:Cyclooxygenase Inhibitors / Q000138:chemical synthesis*; D007527:Isoenzymes / Q000187:drug effects*; D009682:Magnetic Resonance Spectroscopy; D011451:Prostaglandin-Endoperoxide Synthases / Q000187:drug effects*; D011725:Pyridines / Q000138:chemical synthesis
chemical_list: D000894:Anti-Inflammatory Agents, Non-Steroidal; D052246:Cyclooxygenase 2 Inhibitors; D016861:Cyclooxygenase Inhibitors; D007527:Isoenzymes; D011725:Pyridines; D051546:Cyclooxygenase 2; D011451:Prostaglandin-Endoperoxide Synthases