Potassium Phosphate, Tribasic → HCID 25022899, compound

HRID 1516688Notes

Reaction equation

HRID 1516688 reaction equation
FC(F)(F)S(O[C:7]1[C:16]([C:17](=[O:28])[C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=2)=[C:15]([CH:29]2[CH2:33][CH2:32][CH2:31][CH2:30]2)[CH:14]=[C:13]2[C:8]=1[C:9](=[O:36])[CH2:10][C:11]([CH3:35])([CH3:34])[O:12]2)(=O)=O.[F:39][C:40]1[CH:45]=[CH:44][C:43](B(O)O)=[CH:42][CH:41]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:29]1([C:15]2[CH:14]=[C:13]3[C:8]([C:9](=[O:36])[CH2:10][C:11]([CH3:34])([CH3:35])[O:12]3)=[C:7]([C:43]3[CH:44]=[CH:45][C:40]([F:39])=[CH:41][CH:42]=3)[C:16]=2[C:17](=[O:28])[C:18]2[CH:19]=[CH:20][C:21]([C:24]([F:26])([F:27])[F:25])=[CH:22][CH:23]=2)[CH2:30][CH2:31][CH2:32][CH2:33]1

Participants

5

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 2856454-Fluorophenylboronic acidHCID 58002945HCID 58002945, compound

Product 1

HCID 25022899HCID 25022899, compound

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

In a flask which had been dried by heating, 250 mg (0.44 mmol) of 7-cyclopentyl-2,2-dimethyl-4-oxo-6-[4-(trifluoromethyl)benzoyl]-3,4-dihydro-2H-chromen-5-yl trifluoromethanesulfonate (Example 10A), 81 mg (0.58 mmol) of 4-fluorophenylboronic acid, 160 mg (0.75 mmol) of potassium phosphate and 56 mg (0.05 mmol) of tetrakis(triphenylphosphine)palladium(0) are initially charged, and the apparatus is flushed by repeated evacuation and venting with argon. 4 ml of dioxane are then added, the apparatus is closed and the reaction mixture is heated under reflux overnight. The mixture is cooled and filtered through a layer of silica gel, the filter cake is washed thoroughly with ethyl acetate and the filtrate is concentrated. The crude product is purified on silica gel (mobile phase: cyclohexane→cyclohexane/ethyl acetate 10:1→5:1). This gives 194 mg (86% of theory) of the title compound.

Workup

  1. customIn a flask which had been dried
  2. temperatureby heating
  3. customthe apparatus is flushed
  4. addition4 ml of dioxane are then added
  5. customthe apparatus is closed
  6. temperaturethe reaction mixture is heated
  7. temperatureunder reflux overnight
  8. temperatureThe mixture is cooled
  9. filtrationfiltered through a layer of silica gel
  10. washthe filter cake is washed thoroughly with ethyl acetate
  11. concentrationthe filtrate is concentrated
  12. customThe crude product is purified on silica gel (mobile phase: cyclohexane→cyclohexane/ethyl acetate 10:1→5:1)

Sources & evidence

ORD record
ord-b0efc3adb1994e02abb2fbcda12aeb4b
Source dataset
uspto-grants-2012_07
Patent number
US08227511B2

Reaction notes

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