Asymmetric Fluorination Approach to the Scalable Synthesis of a SYK Inhibitor
Publication type: Journal Article
Publication date: 2015-06-25
scimago Q1
wos Q1
SJR: 0.865
CiteScore: 5.4
Impact factor: 3.5
ISSN: 10836160, 1520586X
Organic Chemistry
Physical and Theoretical Chemistry
Abstract
A large-scale process for the synthesis of SYK inhibitor 1 has been developed and used to deliver multi-kilogram yields of this active pharmaceutical ingredient. Integral to the scalable process is a combined chiral auxiliary and chiral catalyst mediated diastereoselective fluorination. Safe processes for BH3·DMS-mediated reduction of ester and amide functions and azide introduction, and a robust Suzuki–Miyaura coupling of a pyrazyl boronate with chloronapthyridine, are described.
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23
Total citations:
23
Citations from 2024:
3
(13.05%)
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GOST
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Curtis N. R. et al. Asymmetric Fluorination Approach to the Scalable Synthesis of a SYK Inhibitor // Organic Process Research and Development. 2015. Vol. 19. No. 7. pp. 865-871.
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Curtis N. R., Davies S. H., Gray M., Leach S. G., Mckie R. A., Vernon L. E., Walkington A. J. Asymmetric Fluorination Approach to the Scalable Synthesis of a SYK Inhibitor // Organic Process Research and Development. 2015. Vol. 19. No. 7. pp. 865-871.
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RIS
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TY - JOUR
DO - 10.1021/acs.oprd.5b00131
UR - https://doi.org/10.1021/acs.oprd.5b00131
TI - Asymmetric Fluorination Approach to the Scalable Synthesis of a SYK Inhibitor
T2 - Organic Process Research and Development
AU - Curtis, Neil R
AU - Davies, Suzanne H
AU - Gray, Matthew
AU - Leach, Stuart G
AU - Mckie, Ross A
AU - Vernon, Lois E
AU - Walkington, Andrew J.
PY - 2015
DA - 2015/06/25
PB - American Chemical Society (ACS)
SP - 865-871
IS - 7
VL - 19
SN - 1083-6160
SN - 1520-586X
ER -
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BibTex (up to 50 authors)
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@article{2015_Curtis,
author = {Neil R Curtis and Suzanne H Davies and Matthew Gray and Stuart G Leach and Ross A Mckie and Lois E Vernon and Andrew J. Walkington},
title = {Asymmetric Fluorination Approach to the Scalable Synthesis of a SYK Inhibitor},
journal = {Organic Process Research and Development},
year = {2015},
volume = {19},
publisher = {American Chemical Society (ACS)},
month = {jun},
url = {https://doi.org/10.1021/acs.oprd.5b00131},
number = {7},
pages = {865--871},
doi = {10.1021/acs.oprd.5b00131}
}
Cite this
MLA
Copy
Curtis, Neil R., et al. “Asymmetric Fluorination Approach to the Scalable Synthesis of a SYK Inhibitor.” Organic Process Research and Development, vol. 19, no. 7, Jun. 2015, pp. 865-871. https://doi.org/10.1021/acs.oprd.5b00131.