A practical synthesis of a COX-2-specific inhibitor

I. W. Davies; J. F. Marcoux; E. G. Corley; M. Journet; D. W. Cai; M. Palucki; J. Wu; R. D. Larsen; K. Rossen; P. J. Pye; L. DiMichele; P. Dormer; P. J. Reider

doi:10.1021/jo000870z

A practical synthesis of a COX-2-specific inhibitor

I. W. Davies
, J. F. Marcoux
, E. G. Corley
, M. Journet
, D. W. Cai
, M. Palucki
, J. Wu
, R. D. Larsen
, K. Rossen
, P. J. Pye
, L. DiMichele
, P. Dormer
, P. J. Reider

Research output: Contribution to journal › Article › peer-review

100 Scopus citations

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.

Original language	English (US)
Pages (from-to)	8415-8420
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	65
Issue number	25
DOIs	https://doi.org/10.1021/jo000870z
State	Published - Dec 15 2000
Externally published	Yes

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1021/jo000870z

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@article{7355a6fabdc9442cb68598544c7fe0f0,

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.",

author = "Davies, \{I. W.\} and Marcoux, \{J. F.\} and Corley, \{E. G.\} and M. Journet and Cai, \{D. W.\} and M. Palucki and J. Wu and Larsen, \{R. D.\} and K. Rossen and Pye, \{P. J.\} and L. DiMichele and P. Dormer and Reider, \{P. J.\}",

year = "2000",

month = dec,

day = "15",

doi = "10.1021/jo000870z",

language = "English (US)",

volume = "65",

pages = "8415--8420",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "25",

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TY - JOUR

T1 - A practical synthesis of a COX-2-specific inhibitor

AU - Davies, I. W.

AU - Marcoux, J. F.

AU - Corley, E. G.

AU - Journet, M.

AU - Cai, D. W.

AU - Palucki, M.

AU - Wu, J.

AU - Larsen, R. D.

AU - Rossen, K.

AU - Pye, P. J.

AU - DiMichele, L.

AU - Dormer, P.

AU - Reider, P. J.

PY - 2000/12/15

Y1 - 2000/12/15

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/0034670533

UR - https://www.scopus.com/pages/publications/0034670533#tab=citedBy

U2 - 10.1021/jo000870z

DO - 10.1021/jo000870z

M3 - Article

C2 - 11112557

AN - SCOPUS:0034670533

SN - 0022-3263

VL - 65

SP - 8415

EP - 8420

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 25

ER -

A practical synthesis of a COX-2-specific inhibitor

Abstract

All Science Journal Classification (ASJC) codes

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