Title:
METHOD OF RAPID METHYLATION OF ALKENE COMPOUND AND KIT FOR PET TRACER PREPARATION USING THE SAME
Document Type and Number:
WIPO Patent Application WO/2007/046258
Kind Code:
A1
Abstract:
[PROBLEMS] To provide a method of rapid alkene compound methylation which is applicable to the preparation of a PET tracer and which enables an alkene compound to be rapidly methylated through cross coupling between SP2 (alkenyl) and SP3 (alkyl) carbon atoms in high yield. [MEANS FOR SOLVING PROBLEMS] Methyl iodide and an alkenyltrialkylstannane are subjected to cross coupling in an aprotic polar solvent in the presence of a complex of palladium having a valence of 0, a phosphine ligand, a cuprous halide, and a carbonate and/or alkali metal fluoride.
Inventors:
SUZUKI MASAAKI (JP)
HOSOYA TAKAMITSU (JP)
HOSOYA TAKAMITSU (JP)
Application Number:
PCT/JP2006/320104
Publication Date:
April 26, 2007
Filing Date:
October 06, 2006
Export Citation:
Assignee:
UNIV GIFU (JP)
SUZUKI MASAAKI (JP)
HOSOYA TAKAMITSU (JP)
SUZUKI MASAAKI (JP)
HOSOYA TAKAMITSU (JP)
International Classes:
C07C1/32; C07C11/02; C07C11/12; C07C13/20; C07C15/02; C07C29/32; C07C33/03; C07C45/68; C07C47/21; C07C49/603; C07C67/343; C07C69/587; C07B59/00; C07B61/00; G01T1/161
Other References:
SUZUKI M. ET AL.: "Rapid Coupling of Methyl Iodide with Aryltributylstannanes Mediated by Palladium(0) Complexes: A General Protocol for the Synthesis of 11CH3-Labeled PET Tracers", CHEM. EUR. J., vol. 3, no. 12, 1997, pages 2039 - 2042, XP003012118
SUZUKI M. ET AL.: "Rapid Methylation for the Synthesis of a 11C-Labeled Tolylisocarbacyclin Imaging the IP2 Receptor in a Living Human Brain", TETRAHEDRON, vol. 56, 2000, pages 8263 - 8273, XP004218732
MEE S. ET AL.: "Stille Coupling Made Easier-The Synergic Effect of Copper(I) Salts and the Fluoride", ANGEW. CHEM. INT. ED., vol. 43, 2004, pages 1132 - 1136, XP003012119
MEE S.P. ET AL.: "Significant Enhancement of the Stille Reaction with a New Combination of Reagents-Copper(I) Indide with Cesium fluoride", CHEM. EUR. J., vol. 11, no. 11, 20 May 2005 (2005-05-20), pages 3294 - 3308, XP003012120
FUWA H. ET AL.: "Total Synthesis of (-)-Gambierol", J. AM. CHEM. SOC., vol. 124, 2002, pages 14983 - 14992, XP003012121
COCKERILL G. ET AL.: "Facile syntheses of building blocks for the construction of phosphotyrosine mimetics", J. CHEM. SOC. PERKIN TRANS., vol. 1, 2000, pages 2591 - 2599, XP002287092
See also references of EP 1947074A4
SUZUKI M. ET AL.: "Rapid Methylation for the Synthesis of a 11C-Labeled Tolylisocarbacyclin Imaging the IP2 Receptor in a Living Human Brain", TETRAHEDRON, vol. 56, 2000, pages 8263 - 8273, XP004218732
MEE S. ET AL.: "Stille Coupling Made Easier-The Synergic Effect of Copper(I) Salts and the Fluoride", ANGEW. CHEM. INT. ED., vol. 43, 2004, pages 1132 - 1136, XP003012119
MEE S.P. ET AL.: "Significant Enhancement of the Stille Reaction with a New Combination of Reagents-Copper(I) Indide with Cesium fluoride", CHEM. EUR. J., vol. 11, no. 11, 20 May 2005 (2005-05-20), pages 3294 - 3308, XP003012120
FUWA H. ET AL.: "Total Synthesis of (-)-Gambierol", J. AM. CHEM. SOC., vol. 124, 2002, pages 14983 - 14992, XP003012121
COCKERILL G. ET AL.: "Facile syntheses of building blocks for the construction of phosphotyrosine mimetics", J. CHEM. SOC. PERKIN TRANS., vol. 1, 2000, pages 2591 - 2599, XP002287092
See also references of EP 1947074A4
Attorney, Agent or Firm:
KONISHI, Tomimasa et al. (17-12 Marunouchi 2-chome, Naka-k, Nagoya-shi Aichi 02, JP)
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