NUCLEOPHILIC FLUORINATION OF AROMATIC COMPOUNDS

WIPO Patent Application WO/2010/008522

A3

Iodylbenzene derivatives substituted with electron donating as well as electron withdrawing groups on the aromatic ring are used as precursors in aromatic nucleophilic substitution reactions. The iodyl group (IO2) is regiospecifically substituted by nucleophilic fluoride to provide the corresponding fluoroaryl derivatives. No-carrier-added [F-18] fluoride ion derived from anhydrous [F- 18]KF/Kryptofix, [F-18]CsF or a quaternary ammonium fluoride (e.g., Me4NF, Et4NF, n-Bu4NF, (PhCH2)4NF) exclusively substitutes the iodyl moiety in these derivatives and provides high specific activity F- 18 labeled fluoroaryl analogs. Iodyl derivatives of a benzothiazole analog and 6-iodyl-L-dopa derivatives have been synthesized as precursors and have been used in the preparation of no-carrier-added [F-18]fluorobenzothiazole as well as 6-[F-18]fluoro-L-dopa.

SATYAMURTHY NAGICHETTIAR (US)
BARRIO JORGE R (US)

PCT/US2009/004063

March 18, 2010

July 13, 2009

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UNIV CALIFORNIA (US)
SATYAMURTHY NAGICHETTIAR (US)
BARRIO JORGE R (US)

C07B59/00; C07C269/06; C07D233/32; C07D263/14; C07D263/18; C07D277/66

WO2005097713A1

2005-10-20

TIERLING T ET AL: "A new nucleophilic asymmetric synthesis of 6-[18F]Fluoro-DOPA", JOURNAL OF LABELLED COMPOUNDS AND RADIOPHARMACEUTICALS, JOHN WILEY, CHICHESTER, GB, vol. 44, no. suppl. 1, 1 January 2001 (2001-01-01), pages 145 - 146, XP009113825, ISSN: 0362-4803
S. RANGANATHAN ET AL.: "A remarkably close ozone equivalent", TETRAHEDRON, vol. 40, no. 16, 1984, pages 3145 - 3151, XP002552867

RAM, Michael, J. et al. (Suite 215Westlake Village, CA, US)

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