A ~(11)C-Methyl stannane (5-[~(11)C]methyl-l-aza-5-stanna-bicyclo[3.3.3]undecane) for use in palladium-mediated [11C]C-C bond forming reactions with organohalides

摘要

The synthesis of a ~(11)C-labelled methyl stannane, (5-[~(11)C]methyl-l-aza-5-stanna-bicyclo[3.3.3]undecane (2)), and its use in palladium-mediated Stille reactions to form [~(11)C]C-C bonds are described. Stannane 2 was synthesized from iodo[~(11)C]methane, 5-chloro-l-aza-5-stanna-bicyclo[3.3.3]undecane 1 and butyl lithium in 20-90% decay-corrected radiochemical yield starting from iodo[~(11)C]methane. Subsequent reaction with a series of substituted aryl and vinyl halides produced the corresponding [~(11)CJmethylated products 3-5 in up to 90% decay-corrected radiochemical yield from the crude 2. The total synthesis time, including purification, was 25-30 min from end of radionuclide production.