Targeted, metal-catalyzed fluorination of complex compounds with fluoride ion via decarboxylation

Patent metadata

Field	Value
Publication number	US-10974235-B2
Application number	US-201916702014-A
Country	US
Kind code	B2
Filing date	Dec 3, 2019
Priority date	Aug 19, 2011
Publication date	Apr 13, 2021
Grant date	Apr 13, 2021

Abstract

Methods of preparing fluorinated compounds by carboxylative fluorination using fluoride are contained herein. Fluorinated compounds are provided. Methods of using fluorinated compounds are contained herein.

First claim

What is claimed is:

1. A method of targeted fluorination of a compound containing a carboxyl group, the method comprising combining the compound containing a carboxyl group, a nucleophilic fluoride source, a solvent and an iodine (III) oxidant to form a mono-fluoro-aryl iodine-(III) carboxylate and then combining the mono-fluoro-aryl iodine-(III) carboxylate with a manganese catalyst.

2. The method of claim 1 , wherein the manganese catalyst is a manganese porphyrin or a manganese salen.

3. The method of claim 1 further comprising maintaining the mono-fluoro-aryl iodine-(III) carboxylate at a temperature from 25° C. to 80° C.

4. The method of claim 1 , wherein the nucleophilic fluoride source is trialkyl amine trihydrofluoride.

5. The method of claim 4 , wherein the trialkyl amine trihydrofluoride is triethylamine trihydrofluoride.

6. The method of claim 1 , wherein the step of combining is performed under an inert atmosphere.

7. The method of claim 1 , wherein the nucleophilic fluoride source is [ 18 F]-fluoride.

8. The method of claim 1 , wherein prior to the step of mixing, the method comprises obtaining an aqueous [ 18 F] fluoride solution from a cyclotron, loading the aqueous [ 18 F] fluoride solution onto an ion exchange cartridge and releasing the [ 18 F] fluoride from the ion exchange cartridge with an alkaline solution.

Assignees

• Univ Princeton

Inventors

• Groves John T
• Huang Xiongyi

Classifications

• A61K51/0423 Primary

  having two or more oxygen atoms in the same ring, e.g. crown ethers, guanadrel · CPC title

• B01J31/04

  containing carboxylic acids or their salts {(B01J31/0277 - B01J31/0298 take precedence; multi-metal carboxylate complexes like Pd (II) acetate, i.e. Pd3 (OAc) 6 or Cr(II)acetate, i.e. Cr2(OAc)4 B01J31/2226)} · CPC title

• C07C41/22

  by introduction of halogens; by substitution of halogen atoms by other halogen atoms · CPC title

• B01J2231/70

  Oxidation reactions, e.g. epoxidation, (di)hydroxylation, dehydrogenation and analogues · CPC title

• C07C2603/74

  Adamantanes · CPC title