Potassium Carbonate → HCID 68422074, compound

HRID 1610122Notes

Reaction equation

HRID 1610122 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[C:5]1[CH:10]=[C:9](I)[C:8]([F:12])=[CH:7][C:6]=1[NH:13][C:14](=[O:16])[CH3:15])[CH3:2].[C:18](=[O:21])([O-])[O-].[K+].[K+].[F:24][C:25]1[CH:26]=[C:27](B(O)O)[CH:28]=[CH:29][CH:30]=1.[C]=O>C1(OC)C=CC=CC=1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[CH2:1]([O:3][C:4](=[O:17])[C:5]1[CH:10]=[C:9]([C:18](=[O:21])[C:29]2[CH:28]=[CH:27][CH:26]=[C:25]([F:24])[CH:30]=2)[C:8]([F:12])=[CH:7][C:6]=1[NH:13][C:14](=[O:16])[CH3:15])[CH3:2]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 27339863-Fluorophenylboronic acidHCID 68420186HCID 68420186, compoundHCID 178418416HCID 178418416, compound2×

Product 1

HCID 68422074HCID 68422074, compoundYield 29.1%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 7519AnisoleSolvent

Procedure

A total of 812 mg of 2-acetylamino-4-fluoro-5-iodo-benzoic acid ethyl ester obtained in Production Example II-7-c was dissolved in 13.9 ml of anisole, and 956 mg of potassium carbonate, 356 mg of 3-fluorophenyl-boronic acid and 49 mg of bis(triphenylphosphine)palladium dichloride were added. After replacing the inside atmosphere of the reaction system with carbon monoxide gas, the mixture was stirred at 80° C. in an atmosphere of carbon monoxide (normal pressure) for 14 hours. After cooling to room temperature and replacing the inside atmosphere of the reaction system with nitrogen gas, water was added and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with brine, dried over magnesium sulfate and the solvent was evaporated. The residue was purified and separated by silica gel column chromatography (ethyl acetate:hexane=1:5), to give 234 mg of the title compound as pale yellow crystals.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe resulting organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent was evaporated
  6. customThe residue was purified
  7. customseparated by silica gel column chromatography (ethyl acetate:hexane=1:5)

Sources & evidence

ORD record
ord-5c19fb5bc29149cea9b9c8e4a62a7c67
Source dataset
uspto-grants-2006_01
Patent number
US06982274B2

Reaction notes

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