Route Design and Development of a MET Kinase Inhibitor: A Copper-Catalyzed Preparation of an N1-Methylindazole
Neil J Kallman
1
,
Chin Liu
1
,
Matthew H Yates
1
,
Ryan J Linder
1
,
J Craig Ruble
1
,
Eugene F Kogut
1
,
Lawrence E Patterson
1
,
Dana L T Laird
1
,
Marvin M Hansen
1
1
Lilly Research Laboratories, Eli Lilly and Company, Lilly Corporate
Center, Indianapolis, Indiana 46285, United States
|
Publication type: Journal Article
Publication date: 2014-03-18
scimago Q1
wos Q1
SJR: 0.865
CiteScore: 5.4
Impact factor: 3.5
ISSN: 10836160, 1520586X
Organic Chemistry
Physical and Theoretical Chemistry
Abstract
The synthesis of a MET kinase inhibitor in an overall yield of 22% was achieved over eight steps starting with 3-hydroxybenzaldehyde, an improvement from the initial 12-step process with a 5.4% yield. Highlights of the process chemistry design and development are a Cu-catalyzed cyclization to form an important N1-methylindazole ring, a selective nitro reduction in the presence of an aryl bromide, a late-stage Suzuki cross-coupling, and a base-promoted Boc deprotection to form the desired drug candidate.
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Total citations:
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GOST
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Kallman N. J. et al. Route Design and Development of a MET Kinase Inhibitor: A Copper-Catalyzed Preparation of an N1-Methylindazole // Organic Process Research and Development. 2014. Vol. 18. No. 4. pp. 501-510.
GOST all authors (up to 50)
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Kallman N. J., Liu C., Yates M. H., Linder R. J., Ruble J. C., Kogut E. F., Patterson L. E., Laird D. L. T., Hansen M. M. Route Design and Development of a MET Kinase Inhibitor: A Copper-Catalyzed Preparation of an N1-Methylindazole // Organic Process Research and Development. 2014. Vol. 18. No. 4. pp. 501-510.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/op400317z
UR - https://doi.org/10.1021/op400317z
TI - Route Design and Development of a MET Kinase Inhibitor: A Copper-Catalyzed Preparation of an N1-Methylindazole
T2 - Organic Process Research and Development
AU - Kallman, Neil J
AU - Liu, Chin
AU - Yates, Matthew H
AU - Linder, Ryan J
AU - Ruble, J Craig
AU - Kogut, Eugene F
AU - Patterson, Lawrence E
AU - Laird, Dana L T
AU - Hansen, Marvin M
PY - 2014
DA - 2014/03/18
PB - American Chemical Society (ACS)
SP - 501-510
IS - 4
VL - 18
SN - 1083-6160
SN - 1520-586X
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2014_Kallman,
author = {Neil J Kallman and Chin Liu and Matthew H Yates and Ryan J Linder and J Craig Ruble and Eugene F Kogut and Lawrence E Patterson and Dana L T Laird and Marvin M Hansen},
title = {Route Design and Development of a MET Kinase Inhibitor: A Copper-Catalyzed Preparation of an N1-Methylindazole},
journal = {Organic Process Research and Development},
year = {2014},
volume = {18},
publisher = {American Chemical Society (ACS)},
month = {mar},
url = {https://doi.org/10.1021/op400317z},
number = {4},
pages = {501--510},
doi = {10.1021/op400317z}
}
Cite this
MLA
Copy
Kallman, Neil J., et al. “Route Design and Development of a MET Kinase Inhibitor: A Copper-Catalyzed Preparation of an N1-Methylindazole.” Organic Process Research and Development, vol. 18, no. 4, Mar. 2014, pp. 501-510. https://doi.org/10.1021/op400317z.