Improved syntheses of precursors for PET radioligands [18F]XTRA and [18F]AZAN

Yongjun Gao; Haofan Wang; Ronnie C. Mease; Martin G. Pomper; Andrew G. Horti

doi:10.1016/j.tetlet.2010.08.001

Improved syntheses of precursors for PET radioligands [¹⁸F]XTRA and [¹⁸F]AZAN

Yongjun Gao, Haofan Wang, Ronnie C. Mease, Martin G. Pomper, Andrew G. Horti

School of Medicine

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

5 Scopus citations

Abstract

Improved syntheses of 7-methyl-2-exo-[3′-(2-bromopyridin-3-yl)- 5′-pyridinyl]-7-azabicyclo[2.2.1]heptanes (3) and 7-methyl-2-exo-[3'-(6- bromopyridin-2-yl)-5′-pyridinyl]-7-azabicyclo[2.2.1]heptanes (4), precursors for PET radioligands [¹⁸F]XTRA (1) and [ ¹⁸F]AZAN (2), involving a key Stille coupling step followed by deprotection of Boc group and N-methylation are described. The new synthetic procedures provided the title compounds in more than 40% overall yields.

Original language	English (US)
Pages (from-to)	5333-5335
Number of pages	3
Journal	Tetrahedron Letters
Volume	51
Issue number	40
DOIs	https://doi.org/10.1016/j.tetlet.2010.08.001
State	Published - Oct 6 2010

Keywords

N-Methylation
PET radioligand
Stille coupling
nAChR

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tetlet.2010.08.001

Cite this

@article{ef96eedbd1a3455fa21f0a428bbdd300,

title = "Improved syntheses of precursors for PET radioligands [18F]XTRA and [18F]AZAN",

abstract = "Improved syntheses of 7-methyl-2-exo-[3′-(2-bromopyridin-3-yl)- 5′-pyridinyl]-7-azabicyclo[2.2.1]heptanes (3) and 7-methyl-2-exo-[3'-(6- bromopyridin-2-yl)-5′-pyridinyl]-7-azabicyclo[2.2.1]heptanes (4), precursors for PET radioligands [18F]XTRA (1) and [ 18F]AZAN (2), involving a key Stille coupling step followed by deprotection of Boc group and N-methylation are described. The new synthetic procedures provided the title compounds in more than 40% overall yields.",

keywords = "N-Methylation, PET radioligand, Stille coupling, nAChR",

author = "Yongjun Gao and Haofan Wang and Mease, {Ronnie C.} and Pomper, {Martin G.} and Horti, {Andrew G.}",

note = "Funding Information: This research was supported by the National Institutes of Health ( DA020777 ) (A.G.H.). Y.G. thanks NARSAD for a Young Investigator Award. ",

year = "2010",

month = oct,

day = "6",

doi = "10.1016/j.tetlet.2010.08.001",

language = "English (US)",

volume = "51",

pages = "5333--5335",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "40",

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TY - JOUR

T1 - Improved syntheses of precursors for PET radioligands [18F]XTRA and [18F]AZAN

AU - Gao, Yongjun

AU - Wang, Haofan

AU - Mease, Ronnie C.

AU - Pomper, Martin G.

AU - Horti, Andrew G.

N1 - Funding Information: This research was supported by the National Institutes of Health ( DA020777 ) (A.G.H.). Y.G. thanks NARSAD for a Young Investigator Award.

PY - 2010/10/6

Y1 - 2010/10/6

N2 - Improved syntheses of 7-methyl-2-exo-[3′-(2-bromopyridin-3-yl)- 5′-pyridinyl]-7-azabicyclo[2.2.1]heptanes (3) and 7-methyl-2-exo-[3'-(6- bromopyridin-2-yl)-5′-pyridinyl]-7-azabicyclo[2.2.1]heptanes (4), precursors for PET radioligands [18F]XTRA (1) and [ 18F]AZAN (2), involving a key Stille coupling step followed by deprotection of Boc group and N-methylation are described. The new synthetic procedures provided the title compounds in more than 40% overall yields.

AB - Improved syntheses of 7-methyl-2-exo-[3′-(2-bromopyridin-3-yl)- 5′-pyridinyl]-7-azabicyclo[2.2.1]heptanes (3) and 7-methyl-2-exo-[3'-(6- bromopyridin-2-yl)-5′-pyridinyl]-7-azabicyclo[2.2.1]heptanes (4), precursors for PET radioligands [18F]XTRA (1) and [ 18F]AZAN (2), involving a key Stille coupling step followed by deprotection of Boc group and N-methylation are described. The new synthetic procedures provided the title compounds in more than 40% overall yields.

KW - N-Methylation

KW - PET radioligand

KW - Stille coupling

KW - nAChR

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DO - 10.1016/j.tetlet.2010.08.001

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SN - 0040-4039

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SP - 5333

EP - 5335

JO - Tetrahedron Letters

JF - Tetrahedron Letters

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