Potassium Carbonate → HCID 44192797, compound

HRID 1855408Notes

Reaction equation

HRID 1855408 reaction equation
C1CCC(P(C2C(C3C=CC=CC=3)=CC=CC=2)C2CCCCC2)CC1.Cl[C:27]1[N:32]=[C:31]([NH:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:30]=[CH:29][CH:28]=1.[CH3:40][O:41][C:42]1[CH:43]=[C:44]([NH2:54])[CH:45]=[CH:46][C:47]=1[N:48]1[CH:52]=[C:51]([CH3:53])[N:50]=[CH:49]1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH3:40][O:41][C:42]1[CH:43]=[C:44]([NH:54][C:27]2[CH:28]=[CH:29][CH:30]=[C:31]([NH:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[N:32]=2)[CH:45]=[CH:46][C:47]=1[N:48]1[CH:52]=[C:51]([CH3:53])[N:50]=[CH:49]1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 27342162-(Dicyclohexylphosphino)biphenylHCID 454801813-methoxy-4-(4-methyl-1H-imidazol-1-yl)anilineHCID 534103056-chloro-N-phenylpyridin-2-amine

Product 1

HCID 44192797HCID 44192797, compoundYield 23%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of palladium(II)acetate (4 mg; 0.02 mmol) and (2-biphenyl) dicyclohexylphosphine (14 mg; 0.04 mmol) in dioxane (5 mL) was stirred under argon for 10 min at 20° C. (6-Chloro-pyridin-2-yl)-phenyl-amine (100 mg; 0.5 mmol), 3-methoxy-4-(4-methyl-imidazol-1-yl)-phenylamine (99 mg; 0.5 mmol), and potassium carbonate (1.35 g; 10 mmol) were added and the mixture was refluxed under argon for 3 h. After quenching the reaction by addition of water, the mixture was extracted with ethyl acetate. The organic phase was dried over sodium sulfate, concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel using dichloromethane/0-20% methanol as eluent to give the title compound (42 mg, 23%) as a light yellow solid.

Workup

  1. additionwere added
  2. temperaturethe mixture was refluxed under argon for 3 h
  3. customAfter quenching
  4. customthe reaction
  5. extractionthe mixture was extracted with ethyl acetate
  6. dry with materialThe organic phase was dried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-1cf62ca934294d4386fda22f69d3e435
Source dataset
uspto-grants-2015_02
Patent number
US08962834B2

Reaction notes

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