Potassium Acetate → HCID 22329529, compound

HRID 586326Notes

Reaction equation

HRID 586326 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([F:15])=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][N:9]=2)[CH:7]=1.[B:16]1(B2OCC(C)(C)CO2)[O:21]CC(C)(C)C[O:17]1.C([O-])(=O)C.[K+]>O1CCOCC1.CS(C)=O.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C(Cl)Cl.Cl[Pd]Cl.[Fe]>[F:15][C:5]1[CH:4]=[CH:3][C:2]([B:16]([OH:21])[OH:17])=[CH:7][C:6]=1[C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][N:9]=1

Participants

7

Reactant 3

HCID 517044Potassium AcetateHCID 2734316Bis(neopentyl glycolato)diboronHCID 22329485HCID 22329485, compound

Product 1

HCID 22329529HCID 22329529, compound

Reagents, catalysts & solvents 3

HCID 53485975CID 53485975CatalystHCID 679Dimethyl SulfoxideSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
85 °C

Procedure

To 2-(5-bromo-2-fluorophenyl)-5-fluoropyridine (0.94 g, 3.48 mmol) and bis(neopentyl glycolato)diboron (0.943 g) in 1,4-dioxane (12 ml) and dimethylsulfoxide (1.5 ml) was added potassium acetate (0.725 g) and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (100 mg). The mixture was degassed with nitrogen and then stirred at 85° C. for 15 h. On cooling to ambient temperature, 1 N aqueous sodium hydroxide (32 ml) was added and the mixture stirred for 20 min. Diethyl ether was added and the aqueous phase separated and washed with diethyl ether. The organic extracts were washed with water and the combined aqueous phases filtered then acidified to pH 5 by addition of 2 N aqueous hydrochloric acid (18 ml). The resulting white solid was collected by filtration, washed with water and dried in vacuo to afford 4-fluoro-3-(5-fluoropyridin-2-yl)phenylboronic acid: 1H NMR (400 MHz, DMSO-d6) 868.73 (1H, dd, J 2 and 1), 8.33 (1H, dd, J 9 and 2), 8.17 (2H, s), 7.87 (3H, m), 7.31 (1H, dd, J 12 and 8).

Workup

  1. customThe mixture was degassed with nitrogen
  2. temperatureOn cooling to ambient temperature
  3. addition1 N aqueous sodium hydroxide (32 ml) was added
  4. stirringthe mixture stirred for 20 min
  5. additionDiethyl ether was added
  6. customthe aqueous phase separated
  7. washwashed with diethyl ether
  8. washThe organic extracts were washed with water
  9. filtrationthe combined aqueous phases filtered
  10. additionthen acidified to pH 5 by addition of 2 N aqueous hydrochloric acid (18 ml)
  11. filtrationThe resulting white solid was collected by filtration
  12. washwashed with water
  13. customdried in vacuo

Sources & evidence

ORD record
ord-87174f13f451451885452ec78549eccc
Source dataset
uspto-grants-2005_08
Patent number
US06936608B2

Reaction notes

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