A Novel Methodology for Efficient Removal of Residual Palladium from a Product of the Suzuki−Miyaura Coupling with Polymer-Supported Ethylenediamine Derivatives

Autor:	Mamoru Miyazawa, Yoshio Urawa, Katsuyuki Ogura, Naoki Ozeki
Rok vydání:	2003
Předmět:	Organic Chemistry Ethylenediamines Inorganic chemistry chemistry.chemical_element ETHYLENEDIAMINE DERIVATIVES Residual Coupling reaction chemistry.chemical_compound chemistry Bromobenzene Coupling (piping) Physical and Theoretical Chemistry Derivative (chemistry) Nuclear chemistry Palladium
Zdroj:	Organic Process Research & Development. 7:191-195
ISSN:	1520-586X 1083-6160
DOI:	10.1021/op0255682
Popis:	In our investigation to efficiently remove residual palladium from a drug candidate prepared via the Suzuki−Miyaura coupling reaction, it was found that polymer-bound ethylenediamines can absorb both Pd(0) and Pd(II). This property was applied to the removal of residual palladium from the crude 2‘-cyanobiphenyl product (R)-2 obtained by the Suzuki−Miyaura coupling of an optically active bromobenzene derivative (R)-1 with a boronate 3. Treatment with the polymer-bound ethylenediamines reduced the palladium content of the crude product from 2000−3000 to 100−300 ppm. Subsequent purification by salt formation with di-p-toluoyl-d-tartaric acid (DTTA) attained a low palladium content of less than 10 ppm.
Databáze:	OpenAIRE
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