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US 9,957,231 B2Granted
Iodine(II)-mediated radiofluorination
AssigneeThe General Hospital Corporation
InventorsNeil Vasdev, Benjamin H. Rotstein, Nickeisha A. Stephenson, Huan Liang
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Abstract
A process for fluorination of aromatic compounds employing iodonium ylides and applicable to radiofluorination using 18F is described. Processes, intermediates, reagents and radiolabelled compounds are described.
Claims28
A process for fluorodeiodination of an aromatic iodide compound comprising:
- (a) oxidizing an aromatic iodide compound (Ar-I), to form an iodonium compound;
- (b) reacting the iodonium compound with a compound of formula (A):
- to form an iodonium ylide;
- (c) reacting the iodonium ylide with a fluoride source to form an aromatic fluoride compound (Ar-F);
- wherein:
- RA and RB in combination, together with the carbon atom to which RA and RB are attached, form a 3, 4, 5, 6, or 7-membered carbocyclic or a heterocyclic ring containing 3 to 7 carbon atoms and 0, 1, or 2 ring heteroatoms, each independently selected from N, O, and S, wherein the ring formed by the combination of RA and RB is unsubstituted or substituted by 1, 2, or 3 substituents independently selected from halogen, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-6 haloalkyl, C1-6 hydroxyalkyl, and oxo.
3 more elements
A compound of Formula D:
- wherein:
- Ar is an aromatic group;
- and
- RA and RB in combination, together with the carbon atom to which RA and RB are attached, form a 3, 4, 5, 6, or 7-membered carbocyclic or a heterocyclic ring containing 3 to 7 carbon atoms and 0, 1, or 2 ring heteroatoms, each independently selected from N, O, and S, wherein the ring formed by the combination of RA and RB is unsubstituted or substituted by 1, 2, or 3 substituents independently selected from halogen, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-6 haloalkyl, C1-6 hydroxyalkyl, and oxo;
- and
- wherein Ar is connected to the iodonium group through an aromatic ring carbon atom.
3 more elements
Dependencies are inferred from the claim text.