Potassium Phosphate, Tribasic → HCID 67032289, compound

HRID 920558Notes

Reaction equation

HRID 920558 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][CH2:10][B-](F)(F)F.[K+].[O-]P([O-])([O-])=O.[K+].[K+].[K+].[CH2:24]([N:31]1[CH2:36][CH:35]([C:37]2[CH:42]=[CH:41][C:40](Br)=[CH:39][CH:38]=2)[O:34][CH2:33][CH2:32]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC(C)C)=CC=CC=2OC(C)C)CCCCC1>C1(C)C=CC=CC=1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:24]([N:31]1[CH2:32][CH2:33][O:34][CH:35]([C:37]2[CH:42]=[CH:41][C:40]([CH2:10][CH2:9][C:3]3[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=3[Cl:8])=[CH:39][CH:38]=2)[CH2:36]1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 162179852-Dicyclohexylphosphino-2',6'-diisopropoxybiphenylHCID 580978794-Benzyl-2-(4-bromo-phenyl)-morpholineHCID 87091097HCID 87091097, compound

Product 1

HCID 67032289HCID 67032289, compoundYield 54.7%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a degassed solution of potassium[2-(2,6-dichlorophenyl)ethyl]trifluoroborate (0.28 g; 1 mmol) and potassium phosphate tribasic (0.58 g; 2.7 mmol) in toluene (20 mL) and water (4 mL) was added 4-benzyl-6-(4-bromo-phenyl)-morpholine (0.30 g; 0.90 mmol), palladium(II) acetate (6.1 mg; 0.03 mmol), and 2-dicyclohexylphosphino-2′,6′-diisopropoxy-1,1′-biphenyl (25.3 mg; 0.05 mmol). The resulting mixture was heated under reflux, overnight. After cooling to RT, the mixture was concentrated in vacuo and partitioned between EtOAc and 5% aqueous NaHCO3. The organic layer was dried (Na2SO4), filtered, and concentrated in vacuo. The residue was purified by column chromatography (SiO2, Et2O:hexanes 1:1) to afford 4-benzyl-2-{4-[2-(2,6-dichloro-phenyl)-ethyl]-phenyl}-morpholine (0.21 g).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux, overnight
  3. concentrationthe mixture was concentrated in vacuo
  4. custompartitioned between EtOAc and 5% aqueous NaHCO3
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography (SiO2, Et2O:hexanes 1:1)

Sources & evidence

ORD record
ord-b3914ae0336e4f6f97ff8249be6b1f8e
Source dataset
uspto-grants-2016_03
Patent number
US09273017B2

Reaction notes

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