Potassium Phosphate, Tribasic → HCID 87189388, compound

HRID 1893577Notes

Reaction equation

HRID 1893577 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[N:6]([CH2:12][CH:13]([F:15])[F:14])[CH2:5]2.[CH3:16]B1OB(C)OB(C)O1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.[Cl-].[Cl-].[Pd+2].O1CCOCC1>[F:14][CH:13]([F:15])[CH2:12][N:6]1[CH2:5][C:4]2[C:8](=[CH:9][CH:10]=[C:2]([CH3:16])[CH:3]=2)[C:7]1=[O:11]

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 574072TrimethylboroxineHCID 231581115-Bromo-2-(2,2-difluoroethyl)-2,3-dihydro-1H-isoindol-1-one

Product 1

HCID 87189388HCID 87189388, compoundYield 99.5%

Reagents, catalysts & solvents 2

HCID 11556747Bis(tricyclohexylphosphine)palladium(II) DichlorideCatalystHCID 312751,4-DioxaneSolvent

Procedure

The compound (5.77 g, 20.9 mmol) of step B, trimethylboroxine (3.00 ml, 21.6 mmol), bis(tricyclohexylphosphine)palladium(II) dichloride (1.53 g, 2.07 mmol) and 1.27 mol/l aqueous potassium phosphate solution (50 ml, 63.5 mmol) were added to 1,4-dioxane (200 ml), and the mixture was heated under reflux for 110 min. The reaction mixture was cooled to room temperature, and concentrated under reduced pressure. The residue was diluted with ethyl acetate, and the organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the solution was concentrated under reduced pressure. The obtained oil was purified by silica gel column chromatography (NH silica gel use, ethyl acetate-hexane) to give the title compound (4.39 g, yield 99%) as a pale-yellow solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 110 min
  3. concentrationconcentrated under reduced pressure
  4. additionThe residue was diluted with ethyl acetate
  5. washthe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationThe insoluble material was filtered off
  8. concentrationthe solution was concentrated under reduced pressure
  9. customThe obtained oil was purified by silica gel column chromatography (NH silica gel use, ethyl acetate-hexane)

Sources & evidence

ORD record
ord-c4a9b24da6cc495286720a6de99ff2dd
Source dataset
uspto-grants-2013_08
Patent number
US08513235B2

Reaction notes

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