Cesium carbonate → HCID 68502632, compound

HRID 888416Notes

Reaction equation

HRID 888416 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([CH:15]=[C:16](B2OC(C)(C)C(C)(C)O2)[CH:17]=1)[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])(=[O:4])=[O:3].Br[C:28]1[CH:33]=[CH:32][C:31]([F:34])=[CH:30][C:29]=1[F:35].C(=O)([O-])[O-].[Cs+].[Cs+]>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:34][C:31]1[CH:30]=[C:29]([F:35])[CH:28]=[CH:33][C:32]=1[C:16]1[CH:17]=[C:5]([S:2]([CH3:1])(=[O:3])=[O:4])[CH:6]=[C:7]([C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9])[CH:15]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 676741-Bromo-2,4-difluorobenzeneHCID 59539717HCID 59539717, compound

Product 1

HCID 68502632HCID 68502632, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 53485975CID 53485975Catalyst

Conditions

Temperature
120 °C

Procedure

The mixture of tert-butyl 3-(methylsulfonyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (0.125 g, 0.33 mmol), 1-bromo-2,4-difluorobenzene (36.9 μL, 0.33 mmol), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (6.68 mg, 8.2 μmol) and cesium carbonate (0.32 g, 0.98 mmol) was purged with nitrogen. A degas solution of THF (1.6 mL) and water (1.6 mL) was added. The mixture was heated in a microwave reactor at 120° C. for 15 min. The mixture was filtered with Celite. Water was added and the mixture was extracted with ethyl acetate (3×). The combined organic extracts were washed with brine, dried over sodium sulfate, filtered and concentrated. Purification by silica gel chromatography (100% hexanes→70% hexanes/ethyl acetate) gave the title compound (77 mg).

Workup

  1. customwas purged with nitrogen
  2. additionA degas solution of THF (1.6 mL) and water (1.6 mL) was added
  3. filtrationThe mixture was filtered with Celite
  4. additionWater was added
  5. extractionthe mixture was extracted with ethyl acetate (3×)
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customPurification by silica gel chromatography (100% hexanes→70% hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-7326ad5e5229411092f75d881703b4d5
Source dataset
uspto-grants-2012_08
Patent number
US08247401B2

Reaction notes

Loading…