Journal of Organometallic Chemistry p. C33 - C36 (1980)
Update date:2022-08-05
Topics:
Seitz, David E.
Tonnesen, Glenn L.
Hellman, Samuel
Hanson, Robert N.
Adelstein, S. James
A procedure has been developed for the synthesis of iodotamoxifen 3 from tamoxifen 1, an anti-estrogenic agent currently employed in the treatment of breast cancer.Ortho-directed metalation of tamoxifen with sec-butyllithium at -78 deg C followed by addition of tri-n-butyltin chloride gave the stannyl derivative 2 in 98percent isolated yield.Iododestannylation of 2 at 0 deg C with iodine afforded the desired iodotamoxifen 3 in quantitative yield.The dimethylaminoethoxy group appears to be more strongly activating for ortho metalation than methoxy.
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Doi:10.1021/jo00144a026
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