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A Pfizer Case Study: Palladium Removal Using SiliaMetS Thiol After a Buchwald-Hartwig Amination

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SiliaMetS Thiol was employed by researchers at Pfizer for Pd removal during the preparation of a naphthalenopiperazine HCl salt. The product from the Buchwald-Hartwig amination of naphthyl bromide with Boc-piperazine was telescoped as a toluene solution and the Boc protecting group was subsequently cleaved with HCl gas to afford the HCl salt containing over 1,300 ppm Pd.

A water / THF solution of this material was then treated with SiliaMetS Thiol (50 wt %) at 35°C for 17 h and, following crystallization from water / THF.

Conclusion

The HCl salt was obtained with a 90 % yield and with only 2 ppm Pd. This chemistry was demonstrated on a kilogram scale.

J. Magano et al., J. Synth. Commun., 2008, 38, 3631-3639
Research API, Pfizer Global Research and Development, Connecticut, United States
Separation Sciences, Pfizer Global Research and Development, Connecticut, United States
Research API, Pfizer Global Research and Development, Michigan, United States
Supply Chain API, Pfizer Global Research and Development, Michigan, United States

 

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  1. SiliaMetS Thiol (SH) (R51030B)

    SiliaMetS Thiol (SH) (R51030B)

    Our most versatile and robust metal scavenger for a variety of metals under a wide range of conditions.

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