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A 11 C‐Methyl stannane (5‐[ 11 C]methyl‐1‐aza‐5‐stanna‐bicyclo[3.3.3]undecane) for use in palladium‐mediated [ 11 C]C–C bond forming reactions with organohalides
Author(s) -
Forngren Tobias,
Samuelsson Linda,
Långström Bengt
Publication year - 2004
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.798
Subject(s) - stannane , chemistry , bicyclic molecule , palladium , stille reaction , undecane , yield (engineering) , medicinal chemistry , organic chemistry , catalysis , materials science , metallurgy
The synthesis of a 11 C‐labelled methyl stannane, (5‐[ 11 C]methyl‐1‐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‐1‐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 C]methylated 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. Copyright © 2003 John Wiley & Sons, Ltd.