Copper (II) mediated arylation with aryl boronic acids for the N-derivatization of pyrazole libraries

S. Rossiter; C.K. Woo; B. Hartzoulakis; G. Wishart; L. Stanyer; J.W. Labadie; D.L. Selwood

doi:10.1021/cc034065k

Copper (II) mediated arylation with aryl boronic acids for the N-derivatization of pyrazole libraries

S. Rossiter, C.K. Woo, B. Hartzoulakis, G. Wishart, L. Stanyer, J.W. Labadie, D.L. Selwood

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

16 Citations (Scopus)

Abstract

A N-derivatized 3-dimethylaminopropyloxypyrazole library was prepared using solution-phase parallel synthesis. The library was designed using physicochemical constraints designed to remove non-membrane-permeable molecules. Cupric acetate-mediated N-arylation with aryl boronic acids proceeded regioselectively to form the N-2-substituted derivatives. The presence of the 3-dimethylaminopropyloxy group was found to completely control the regioselectivity of the arylation. Presence of a dimethylaminoethyloxy or dimethylaminobutyloxy group gave a lesser degree of regioselectivity. The scope of the method as applied to library synthesis is discussed.

Original language	English
Pages (from-to)	385-390
Journal	Journal of Combinatorial Chemistry
Volume	6
Issue number	3
DOIs	https://doi.org/10.1021/cc034065k
Publication status	Published - 2004

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title = "Copper (II) mediated arylation with aryl boronic acids for the N-derivatization of pyrazole libraries",

abstract = "A N-derivatized 3-dimethylaminopropyloxypyrazole library was prepared using solution-phase parallel synthesis. The library was designed using physicochemical constraints designed to remove non-membrane-permeable molecules. Cupric acetate-mediated N-arylation with aryl boronic acids proceeded regioselectively to form the N-2-substituted derivatives. The presence of the 3-dimethylaminopropyloxy group was found to completely control the regioselectivity of the arylation. Presence of a dimethylaminoethyloxy or dimethylaminobutyloxy group gave a lesser degree of regioselectivity. The scope of the method as applied to library synthesis is discussed. ",

author = "S. Rossiter and C.K. Woo and B. Hartzoulakis and G. Wishart and L. Stanyer and J.W. Labadie and D.L. Selwood",

note = "Original article can be found at: http://pubs.acs.org/journal/jcchff Copyright American Chemical Society DOI: 10.1021/cc034065k [Full text of this article is not available in the UHRA]",

year = "2004",

doi = "10.1021/cc034065k",

language = "English",

volume = "6",

pages = "385--390",

journal = "Journal of Combinatorial Chemistry",

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TY - JOUR

T1 - Copper (II) mediated arylation with aryl boronic acids for the N-derivatization of pyrazole libraries

AU - Rossiter, S.

AU - Woo, C.K.

AU - Hartzoulakis, B.

AU - Wishart, G.

AU - Stanyer, L.

AU - Labadie, J.W.

AU - Selwood, D.L.

N1 - Original article can be found at: http://pubs.acs.org/journal/jcchff Copyright American Chemical Society DOI: 10.1021/cc034065k [Full text of this article is not available in the UHRA]

PY - 2004

Y1 - 2004

N2 - A N-derivatized 3-dimethylaminopropyloxypyrazole library was prepared using solution-phase parallel synthesis. The library was designed using physicochemical constraints designed to remove non-membrane-permeable molecules. Cupric acetate-mediated N-arylation with aryl boronic acids proceeded regioselectively to form the N-2-substituted derivatives. The presence of the 3-dimethylaminopropyloxy group was found to completely control the regioselectivity of the arylation. Presence of a dimethylaminoethyloxy or dimethylaminobutyloxy group gave a lesser degree of regioselectivity. The scope of the method as applied to library synthesis is discussed.

AB - A N-derivatized 3-dimethylaminopropyloxypyrazole library was prepared using solution-phase parallel synthesis. The library was designed using physicochemical constraints designed to remove non-membrane-permeable molecules. Cupric acetate-mediated N-arylation with aryl boronic acids proceeded regioselectively to form the N-2-substituted derivatives. The presence of the 3-dimethylaminopropyloxy group was found to completely control the regioselectivity of the arylation. Presence of a dimethylaminoethyloxy or dimethylaminobutyloxy group gave a lesser degree of regioselectivity. The scope of the method as applied to library synthesis is discussed.

U2 - 10.1021/cc034065k

DO - 10.1021/cc034065k

M3 - Article

VL - 6

SP - 385

EP - 390

JO - Journal of Combinatorial Chemistry

JF - Journal of Combinatorial Chemistry

SN - 1520-4766

IS - 3

ER -

Copper (II) mediated arylation with aryl boronic acids for the N-derivatization of pyrazole libraries

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