1-Bromo-3,5-difluorobenzene → HCID 70011073, compound

HRID 1368779Notes

Reaction equation

HRID 1368779 reaction equation
[CH3:1][C@H:2]1[CH2:7][NH:6][CH2:5][CH2:4][NH:3]1.[F:8][C:9]1[CH:10]=[C:11](Br)[CH:12]=[C:13]([F:15])[CH:14]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1>[F:8][C:9]1[CH:10]=[C:11]([N:6]2[CH2:5][CH2:4][NH:3][C@@H:2]([CH3:1])[CH2:7]2)[CH:12]=[C:13]([F:15])[CH:14]=1

Participants

5

Reactant 3

HCID 1363131-Bromo-3,5-difluorobenzeneHCID 27342192-Methylpiperazine, (S)-HCID 23676156Sodium t-butoxide

Product 1

HCID 70011073HCID 70011073, compoundYield 43.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture composed of 2.48 g of (S)-2-methylpiperazine, 3.97 g of 3,5-difluorobromobenzene, 2.76 g of sodium tert-butoxide, 326 mg of dichlorobis[(tri-ortho-tolyl)phosphine]palladium (II) (PdCl2[P(o-tolyl)3]2) and 100 ml of toluene was stirred at 100° C. for 24 hours in an atmosphere of nitrogen. After removal of the insoluble matter by filtration, the filtrate was washed with water and then with saturated brine. The organic layer was dried with anhydrous sodium sulfate and then concentrated under a reduced pressure, the residue was applied to a silica gel column chromatography (270 to 400 mesh, 100 g) and developed with a methanol-chloroform (6:94) mixed solvent, and then the fractions containing the compound of interest were concentrated to obtain 1.89 g of the title compound.

Workup

  1. customAfter removal of the insoluble matter
  2. filtrationby filtration
  3. washthe filtrate was washed with water
  4. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  5. concentrationconcentrated under a reduced pressure
  6. additionmixed solvent
  7. additionthe fractions containing the compound of interest
  8. concentrationwere concentrated

Sources & evidence

ORD record
ord-6eada1ff74df41ffabf16ec8d553aef0
Source dataset
uspto-grants-2003_06
Patent number
US06573377B1

Reaction notes

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