# US 2017/0283441 A1 · Production method for 2-fluoro-4-borono-l-phenylalanine, and precursor of 2-fluoro-4-borono-l-phenylalanine > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2017/0283441 A1 - Document ID: US20170283441A1 - Status: Published application - Kind: A1 - Application number: 15/625,909 - Filed: 2017-06-16 - Published: 2017-10-05 - Earliest claimed: 2013-12-17 - Assignees: Stella Pharma Corporation; Osaka Prefecture University Public Corporation - Applicants: Stella Pharma Corporation; Osaka Prefecture University Public Corporation - Inventors: Hiroshi Takenaka; Yoichiro Ohta; Yusuke Taguchi; Sayuri Ueda; Yuko Ishino; Tomohiro Yoshikawa; Hideki Nakashima; Kohki Uehara; Mitsunori Kirihata - Web page: https://patentgrep.com/patent/US20170283441A1 ## CPC - C07F 5/027: {Organoboranes and organoborohydrides} - C07C 229/36: with at least one amino group and one carboxyl group bound to the same carbon atom of the carbon skeleton - C07C 251/24: having carbon atoms of imino groups bound to carbon atoms of six-membered aromatic rings - C07C 271/22: to carbon atoms of hydrocarbon radicals substituted by carboxyl groups - Y02P 20/55: Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups - C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22) - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS - Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS ## Abstract The present invention involves preparing compounds represented by the following formula: from a compound of the following formula: In these formulae: R1 represents a Br group, an iodine group, a Cl group, an NO2 group, or an NH2 group; R2 represents a halogen group, an NO2 group, an NH2 group, Sn(R6)3, N═N—NR7R8, OSO2R9, N R10R11, phenyliodonium, a heterocyclic group iodine, boric acid, or a borate ester; R30 represents a protective group PG1; R40 or R50 represent hydrogen, a protective group PG2, or C6H5(C6H5)C═N, in which NR40R50 are together. ## Claims ### Claim 1 A method for producing a compound represented by the following formula: (where X represents F or 18F; R30 represents hydrogen or a protecting group PG1 for a carboxyl group; R40 or R50 independently represents hydrogen or a protecting group PG2 for an amino group, or NR40R50 are combined together to form C6H5(C6H5)C═N; and R15 and R16 are combined together with a boron atom to form a ring serving as a protecting group for boron atom, comprising: reacting a compound represented by the following formula: where R1 represents a bromo group, an iodo group, a chloro group, a nitro group, or an amino group; R2 represents a halogen group, a nitro group, an amino group, Sn(R6)3, N═N—NR7R8, OSO2R9, NR10R11, substituted or unsubstituted phenyl iodo, a substituted or unsubstituted heterocyclic iodo group, or boric acid or a boric ester (where R6 represents an alkyl group having 1 to 7 carbon atoms or a benzyl group; R7 and R8 are the same or different, each representing hydrogen, an alkyl group having 1 to 7 carbon atoms, a halogen-substituted alkyl group having 1 to 7 carbon atoms, or an optionally substituted phenyl group, or else R7 and R8 are combined together with N to form a 3- to 7-membered cyclic structure; R9 represents an alkyl group having 1 to 7 carbon atoms, a halogen-substituted alkyl group having 1 to 7 carbon atoms, or an optionally substituted phenyl group; R10 and R11 are the same or different, each representing an alkyl group having 1 to 7 carbon atoms, a halogen-substituted alkyl group having 1 to 7 carbon atoms, or an optionally substituted phenyl group, or else R10 and R11 are combined together with N to form a 3- to 7-membered cyclic structure); and R30, R40, and R50 have the same meaning as described above, wherein said reacting comprises radiating said compound in the presence of a catalyst and a ligand. ### Claim 2 (depends on 1) The method of claim 1, wherein the catalyst is a palladium catalyst. ### Claim 3 (depends on 2) The method of claim 2, wherein the palladium catalyst is selected from the group consisting of a palladium chloride cinnamyl complex, palladium acetate, and trisdibenzylideneacetonedipalladium. ### Claim 4 (depends on 1) The method of claim 1, wherein the radiating comprises microwave radiation. ### Claim 5 (depends on 4) The method of claim 4, wherein the microwave radiation is conducted from room temperature to 200° C. ### Claim 6 (depends on 4) The method of claim 4, wherein the reaction period is from 1 minute to 60 minutes. ### Claim 7 (depends on 1) The method of claim 1, wherein the ligand is a phosphorus-based ligand. ### Claim 8 (depends on 7) The method of claim 7, wherein the phosphorus-based ligand is selected from the group consisting of tricyclohexylphosphine, 2-dicyclohexylphosphino-2,4,6-triisopropylbiphenyl, 2-dicyclohexylphosphino-2,-(N,N)-dimethylaminobiphenyl, 3,5-dimethoxy-2-dicyclohexylphosphino-2,4,6-triisopropylbiphenyl, and 3,5-dimethoxy-2-ditert-butylphosphino-2,4,6-triisopropylbiphenyl. ### Claim 9 (depends on 1) The method of claim 1, wherein the reacting is conducted in the presence of a base. ### Claim 10 (depends on 9) The method of claim 9, wherein the base is selected from the group consisting of lithium hydroxide, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, and trimethylamine. ### Claim 11 (depends on 1) The method of claim 1, wherein the reacting is conducted in a solvent selected from the group consisting of toluene, dioxane, and DMDO.