76070-10-5Relevant articles and documents
IODODESTANNYLATION. POSITION-SPECIFIC SYNTHESIS OF IODOTAMOXIFEN
Seitz, David E.,Tonnesen, Glenn L.,Hellman, Samuel,Hanson, Robert N.,Adelstein, S. James
, p. C33 - C36 (1980)
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.