Potassium Phosphate, Tribasic → HCID 86732661, compound

HRID 523448Notes

Reaction equation

HRID 523448 reaction equation
[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[C:4](B(O)O)=[CH:3][CH:2]=1.Br[C:18]1[CH:23]=[CH:22][C:21]([N:24]2[C:37](=[O:38])[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[C:30]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]2=3)=[CH:20][CH:19]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.O1CCOCC1>[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[C:4]([C:18]2[CH:23]=[CH:22][C:21]([N:24]3[C:37](=[O:38])[C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[C:30]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]3=4)=[CH:20][CH:19]=2)=[CH:3][CH:2]=1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 80271Tri-o-tolylphosphineHCID 2734328Dibenzofuran-4-boronic acidHCID 86732660HCID 86732660, compound

Product 1

HCID 86732661HCID 86732661, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

23 g (110.0 mmol) of 4-dibenzofuranboronic acid, 38 g (110 0 mmol) of 5-(4-bromophenyl)-5H-phenanthridin-6-one and 44.6 g (210.0 mmol) of tripotassium phosphate are suspended in 500 ml of toulene, 500 ml of dioxane and 500 ml of water. 913 mg (3.0 mmol) of tri-o-tolylphosphine and then 112 mg (0.5 mmol) of palladium(II) acetate are added to this suspension, and the reaction mixture is heated under reflux for 16 h. After cooling, the organic phase is separated off, filtered through silica gel, washed three times with 200 ml of water each time and subsequently evaporated to dryness. The residue is recrystallised from toluene and from dichloromethane/isopropanol and finally sublimed in a high vacuum, purity is 99.9%. The yield is 38 g (92 mmol), corresponding to 84% of theory.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureunder reflux for 16 h
  3. temperatureAfter cooling
  4. customthe organic phase is separated off
  5. filtrationfiltered through silica gel
  6. washwashed three times with 200 ml of water each time
  7. customsubsequently evaporated to dryness
  8. customThe residue is recrystallised from toluene and from dichloromethane/isopropanol

Sources & evidence

ORD record
ord-14f476193a3944ad98d8bbe740279aee
Source dataset
uspto-grants-2016_05
Patent number
US09337430B2

Reaction notes

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