Copper-mediated nucleophilic radiobromination of aryl boron precursors: Convenient preparation of a radiobrominated PARP-1 inhibitor

Dong Zhou; Wenhua Chu; Thomas Voller; John A. Katzenellenbogen

doi:10.1016/j.tetlet.2018.04.024

Copper-mediated nucleophilic radiobromination of aryl boron precursors: Convenient preparation of a radiobrominated PARP-1 inhibitor

Dong Zhou
, Wenhua Chu
, Thomas Voller
, John A. Katzenellenbogen

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

26 Scopus citations

Abstract

The copper-mediated nucleophilic radiobromination of aryl boron precursors with a radiobromide ion is a novel radiolabeling method that is efficient and robust. High radiochemical conversion (RCC) was observed using a variety of solvents, temperatures and catalysts. The reaction is also clean and is feasible for purification to obtain high chemical and radiochemical purity. This method provides a very useful route for the preparation of radiobrominated pharmaceuticals, including a radiobromine labeled PARP-1 inhibitor, and it is a valuable addition to the family of copper-mediated radiolabeling processes.

Original language	English
Pages (from-to)	1963-1967
Number of pages	5
Journal	Tetrahedron Letters
Volume	59
Issue number	20
DOIs	https://doi.org/10.1016/j.tetlet.2018.04.024
State	Published - May 16 2018

Keywords

Auger electron radiation
Boron reagents
Bromine-76
Bromine-77
Labeling method
Nucleophilic radiobromination
PET imaging

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10.1016/j.tetlet.2018.04.024

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title = "Copper-mediated nucleophilic radiobromination of aryl boron precursors: Convenient preparation of a radiobrominated PARP-1 inhibitor",

abstract = "The copper-mediated nucleophilic radiobromination of aryl boron precursors with a radiobromide ion is a novel radiolabeling method that is efficient and robust. High radiochemical conversion (RCC) was observed using a variety of solvents, temperatures and catalysts. The reaction is also clean and is feasible for purification to obtain high chemical and radiochemical purity. This method provides a very useful route for the preparation of radiobrominated pharmaceuticals, including a radiobromine labeled PARP-1 inhibitor, and it is a valuable addition to the family of copper-mediated radiolabeling processes.",

keywords = "Auger electron radiation, Boron reagents, Bromine-76, Bromine-77, Labeling method, Nucleophilic radiobromination, PET imaging",

author = "Dong Zhou and Wenhua Chu and Thomas Voller and Katzenellenbogen, \{John A.\}",

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T1 - Copper-mediated nucleophilic radiobromination of aryl boron precursors

T2 - Convenient preparation of a radiobrominated PARP-1 inhibitor

AU - Zhou, Dong

AU - Chu, Wenhua

AU - Voller, Thomas

AU - Katzenellenbogen, John A.

PY - 2018/5/16

Y1 - 2018/5/16

N2 - The copper-mediated nucleophilic radiobromination of aryl boron precursors with a radiobromide ion is a novel radiolabeling method that is efficient and robust. High radiochemical conversion (RCC) was observed using a variety of solvents, temperatures and catalysts. The reaction is also clean and is feasible for purification to obtain high chemical and radiochemical purity. This method provides a very useful route for the preparation of radiobrominated pharmaceuticals, including a radiobromine labeled PARP-1 inhibitor, and it is a valuable addition to the family of copper-mediated radiolabeling processes.

AB - The copper-mediated nucleophilic radiobromination of aryl boron precursors with a radiobromide ion is a novel radiolabeling method that is efficient and robust. High radiochemical conversion (RCC) was observed using a variety of solvents, temperatures and catalysts. The reaction is also clean and is feasible for purification to obtain high chemical and radiochemical purity. This method provides a very useful route for the preparation of radiobrominated pharmaceuticals, including a radiobromine labeled PARP-1 inhibitor, and it is a valuable addition to the family of copper-mediated radiolabeling processes.

KW - Auger electron radiation

KW - Boron reagents

KW - Bromine-76

KW - Bromine-77

KW - Labeling method

KW - Nucleophilic radiobromination

KW - PET imaging

UR - https://www.scopus.com/pages/publications/85045538248

U2 - 10.1016/j.tetlet.2018.04.024

DO - 10.1016/j.tetlet.2018.04.024

M3 - Article

AN - SCOPUS:85045538248

SN - 0040-4039

VL - 59

SP - 1963

EP - 1967

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 20

ER -

Copper-mediated nucleophilic radiobromination of aryl boron precursors: Convenient preparation of a radiobrominated PARP-1 inhibitor

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Keywords

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