Phenylboronic Acid → HCID 58852671, compound

HRID 573001Notes

Reaction equation

HRID 573001 reaction equation
Br[C:2]1[N:7]=[C:6]([C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13](Br)[N:12]=2)([F:10])[CH3:9])[CH:5]=[CH:4][CH:3]=1.[C:18]1(B(O)O)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[F-].[K+]>C1COCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>[C:18]1([C:2]2[N:7]=[C:6]([C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[N:12]=3)([F:10])[CH3:9])[CH:5]=[CH:4][CH:3]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 3

HCID 66827Phenylboronic AcidHCID 522689Potassium FluorideHCID 58852716HCID 58852716, compound

Product 1

HCID 58852671HCID 58852671, compoundYield 88.6%

Reagents, catalysts & solvents 3

HCID 83681Tris(1,1-dimethylethyl)phosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

600 μl (2.6 mmol) of tri-tert-butylphosphine and 449 mg (2.0 mmol) of palladium(II) acetate were added to a degassed suspension of 18.0 g (50 mmol) of 1,1-bis(6-bromo-2-pyridyl)-1-fluoroethane, 24.4 g (200 mmol) of benzeneboronic acid and 19.2 g (330 mmol) of potassium fluoride in 350 ml of THF, and the mixture was heated under reflux for 3 h with stirring. After cooling, the THF was removed under reduced pressure, and the residue was taken up in 500 ml of dichloromethane and washed three times with 300 ml of water. After drying over magnesium sulfate, filtration through silica gel and stripping-off of the solvent, the yellow oil remaining was recrystallised three times from ethanol, giving 15.7 g (44 mmol) of the product, corresponding to a yield of 88.6%, in the form of colourless crystal needles—purity according to 1H-NMR>99%.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 h
  3. temperatureAfter cooling
  4. customthe THF was removed under reduced pressure
  5. washwashed three times with 300 ml of water
  6. dry with materialAfter drying over magnesium sulfate, filtration through silica gel and stripping-off of the solvent
  7. customthe yellow oil remaining was recrystallised three times from ethanol

Sources & evidence

ORD record
ord-e2455030cb49405aa874f46d2552ca65
Source dataset
uspto-grants-2015_05
Patent number
US09029539B2

Reaction notes

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