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

95 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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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",

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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.

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DO - 10.1021/jo000870z

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AN - SCOPUS:0034670533

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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

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