Sodium Carbonate → 5-(2-Fluorophenyl)pyridin-2(1H)-one

HRID 1747794Notes

Reaction equation

HRID 1747794 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5](=[O:8])[NH:6][CH:7]=1.[F:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].[Cl-].[Li+]>[Cl-].[Na+].O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.C(O)C.C1(C)C=CC=CC=1>[F:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:2]1[CH:3]=[CH:4][C:5](=[O:8])[NH:6][CH:7]=1

Participants

10

Reactant 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 5995285-Bromo-2-hydroxypyridineHCID 27343542-Fluorophenylboronic acid

Product 1

HCID 203000835-(2-Fluorophenyl)pyridin-2(1H)-oneYield 5%

Reagents, catalysts & solvents 5

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
100 °C

Procedure

5-Bromopyridin-2(1H)-one (1.04 g), (2-fluorophenyl)boronic acid (0.924 g), sodium carbonate (1.40 g), lithium chloride (0.560 g) and tetrakis(triphenylphosphine)palladium(0) (0.347 g) were suspended in a mixed solvent of toluene (26.4 mL), ethanol (6.6 mL) and water (6.6 mL), and the suspension was stirred at 100° C. for 17 hr under an argon atmosphere. The reaction mixture was cooled to room temperature, diluted with brine, extracted with ethyl acetate, diluted with THF, dried over anhydrous sodium sulfate, filtered, concentrated, and purified by silica gel column chromatography (ethyl acetate/hexane→ethyl acetate/methanol) to give the title compound (0.0563 g).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. additiondiluted with THF
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by silica gel column chromatography (ethyl acetate/hexane→ethyl acetate/methanol)

Sources & evidence

ORD record
ord-64b2d526362140e299911951c3ff6874
Source dataset
uspto-grants-2015_10
Patent number
US09150588B2

Reaction notes

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