Potassium Phosphate, Tribasic → HCID 66880906, compound

HRID 1893570Notes

Reaction equation

HRID 1893570 reaction equation
I[C:2]1[C:10]2[C:5](=[CH:6][C:7]([N+:12]([O-:14])=[O:13])=[C:8]([CH3:11])[CH:9]=2)[N:4]([CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][O:16]2)[N:3]=1.[CH3:21]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>[CH3:21][C:2]1[C:10]2[C:5](=[CH:6][C:7]([N+:12]([O-:14])=[O:13])=[C:8]([CH3:11])[CH:9]=2)[N:4]([CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][O:16]2)[N:3]=1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 574072TrimethylboroxineHCID 66881069HCID 66881069, compound

Product 1

HCID 66880906HCID 66880906, compoundYield 68.4%

Reagents, catalysts & solvents 2

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

Procedure

The compound (5.60 g, 14.5 mmol) of step A, trimethylboroxine (2.20 ml, 15.8 mmol), bis(tricyclohexylphosphine)palladium(II)dichloride (926 mg, 1.25 mmol) and 1.27 mol/l aqueous potassium phosphate solution (35.0 ml, 44.5 mmol) were added to 1,4-dioxane (150 ml), and the mixture was heated under reflux for 18 hr. The reaction mixture was cooled to room temperature, and the solution was 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 to concentrated under reduced pressure. The obtained oil was purified by silica gel column chromatography (ethyl acetate-hexane) to give the title compound (2.73 g, yield 68%) as a yellow solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 18 hr
  3. concentrationthe solution was concentrated 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. concentrationto concentrated under reduced pressure
  9. customThe obtained oil was purified by silica gel column chromatography (ethyl acetate-hexane)

Sources & evidence

ORD record
ord-c6d4250a98ec4a0298cfdc36e406e98a
Source dataset
uspto-grants-2013_08
Patent number
US08513235B2

Reaction notes

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