Potassium Phosphate, Tribasic → HCID 22226913, compound

HRID 1745909Notes

Reaction equation

HRID 1745909 reaction equation
Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([N:12]1[C:16]3[CH:17]=[CH:18][C:19]([O:21][CH2:22][CH2:23][O:24][CH3:25])=[CH:20][C:15]=3[N:14]=[CH:13]1)[CH:8]=[CH:7]2.[OH:26][C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:25][O:24][CH2:23][CH2:22][O:21][C:19]1[CH:18]=[CH:17][C:16]2[N:12]([C:9]3[CH:8]=[CH:7][C:6]4[C:11](=[C:2]([C:30]5[CH:31]=[CH:32][C:27]([OH:26])=[CH:28][CH:29]=5)[CH:3]=[CH:4][CH:5]=4)[N:10]=3)[CH:13]=[N:14][C:15]=2[CH:20]=1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 27343604-Hydroxyphenylboronic acidHCID 22226921HCID 22226921, compound

Product 1

HCID 22226913HCID 22226913, compoundYield 60.3%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
105 °C

Procedure

8-Bromo-2-[5-(2-methoxy-ethoxy)-benzoimidazol-1-yl]-quinoline 61F (585 mg, 1.47 mMol), was dissolved in 10 mL of dioxane under an atmosphere of dry N2. To this solution were added 4-hydroxyphenyl boronic acid (240 mg, 1.74 mMol), potassium phosphate (620 mg, 2.92 mMol) and tetrakis(triphenylphosphine)palladium (0) (85 mg, 0.074 mMol). The reaction mixture was heated to 105° C. and reacted at this temperature for 48 hours. The reaction mixture was then cooled to ambient temperature, concentrated under vacuum and partitioned between DCM and aqueous saturated NaHCO3. The DCM layer was then washed with brine, dried over Na2SO4, filtered and concentrated under vacuum to give a yellow residue. The residue was chromatographed on flash silica gel eluting with MeOH/DCM/NH4OH (297.90.1) to give 365 mg of a white foam as the title compound 61.

Workup

  1. customreacted at this temperature for 48 hours
  2. temperatureThe reaction mixture was then cooled to ambient temperature
  3. concentrationconcentrated under vacuum
  4. custompartitioned between DCM and aqueous saturated NaHCO3
  5. washThe DCM layer was then washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customto give a yellow residue
  10. customThe residue was chromatographed on flash silica gel eluting with MeOH/DCM/NH4OH (297.90.1)

Sources & evidence

ORD record
ord-39465e48e3284dbfbc013650b10a6415
Source dataset
uspto-grants-2006_03
Patent number
US07019147B1

Reaction notes

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