A Novel Methodology for Efficient Removal of Residual Palladium from a Product of the Suzuki−Miyaura Coupling with Polymer-Supported Ethylenediamine Derivatives
2003; American Chemical Society; Volume: 7; Issue: 2 Linguagem: Inglês
10.1021/op0255682
ISSN1520-586X
AutoresYoshio Urawa, Mamoru Miyazawa, Naoki Ozeki, Katsuyuki Ogura,
Tópico(s)Coordination Chemistry and Organometallics
ResumoIn 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.
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