Sodium Carbonate → HCID 59843077, compound

HRID 1878694Notes

Reaction equation

HRID 1878694 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5](=[O:11])[N:6]([CH2:8][CH2:9][OH:10])[CH:7]=1.[F:12][C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[CH:17][CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1>O.[Pd]>[F:12][C:13]1[CH:18]=[C:17]([C:2]2[CH:3]=[CH:4][C:5](=[O:11])[N:6]([CH2:8][CH2:9][OH:10])[CH:7]=2)[CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 27339863-Fluorophenylboronic acidHCID 434194335-bromo-1-(2-hydroxyethyl)pyridin-2(1H)-one

Product 1

HCID 59843077HCID 59843077, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

5-Bromo-1-(2-hydroxyethyl)pyridin-2(1H)-one (100.7 mg, 462 μmol), 3-fluorophenylboronic acid (121.5 mg, 868 μmol), palladium fibercat catalyst (4.11%, 14.1 mg), and sodium carbonate (0.48 ml, 2.0 M in water, 960 μmol) were put in a microwave vial, and then 1,4-dioxane (0.69 ml) was added. The microwave vial was sealed and heated in the CEM microwave at 120° C. and 50 Watts for a 5 minute ramp time and then a 20-minute run time. The reaction was then cooled to room temperature, diluted with water, and extracted with 3:1 CH2Cl2/MeOH. The organic phases were combined, dried over sodium sulfate, filtered, concentrated, and dried under vacuum. The material was used for the next step. MS (ESI pos. ion) m/z (MH+): 234. Calc'd exact mass for C13H12FNO2: 233.

Workup

  1. additionwas added
  2. customThe microwave vial was sealed
  3. customa 20-minute
  4. temperatureThe reaction was then cooled to room temperature
  5. extractionextracted with 3:1 CH2Cl2/MeOH
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customdried under vacuum

Sources & evidence

ORD record
ord-b098af797b8040e58f800b48c1752568
Source dataset
uspto-grants-2012_11
Patent number
US08314087B2

Reaction notes

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