Cesium carbonate → HCID 117824220, compound

HRID 59067Notes

Reaction equation

HRID 59067 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]([O:10][CH2:11][CH3:12])=[CH2:9])[CH:5]=[C:4]([CH:13]([O:15][CH2:16][C:17]([F:20])([F:19])[F:18])[CH3:14])[N:3]=1.[CH3:21][O:22][C:23]1[CH:24]=[C:25]([CH:27]=[CH:28][C:29]=1[N:30]1[CH:34]=[C:33]([CH3:35])[N:32]=[CH:31]1)[NH2:26].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1.C(=O)([O-])[O-].[Cs+].[Cs+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O1CCOCC1>[CH2:11]([O:10][C:8]([C:6]1[CH:5]=[C:4]([CH:13]([O:15][CH2:16][C:17]([F:20])([F:19])[F:18])[CH3:14])[N:3]=[C:2]([NH:26][C:25]2[CH:27]=[CH:28][C:29]([N:30]3[CH:34]=[C:33]([CH3:35])[N:32]=[CH:31]3)=[C:23]([O:22][CH3:21])[CH:24]=2)[N:7]=1)=[CH2:9])[CH3:12]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 27342162-(Dicyclohexylphosphino)biphenylHCID 454801813-methoxy-4-(4-methyl-1H-imidazol-1-yl)anilineHCID 117821238HCID 117821238, compound

Product 1

HCID 117824220HCID 117824220, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
120 °C

Procedure

2-Chloro-4-(1-ethoxyvinyl)-6-(1-(2,2,2-trifluoroethoxy)ethyl)pyrimidine (0.35 g, 1.13 mmol), 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)aniline (0.275 g, 1.35 mmol), palladium(II) acetate (0.038 g, 0.17 mmol), 2-(dicyclohexylphosphino)biphenyl (0.059 g, 0.17 mmol), cesium carbonate (0.734 g, 2.25 mmol) and dioxane (4 mL) were mixed in a vial. The vial was capped, evacuated and flushed with nitrogen. The reaction mixture was heated by microwave irradiation at 120° C. for 2.5 h, cooled and filtered through a pad of silica gel. The pad was eluted with 10% methanol in ethyl acetate. The solvents were evaporated and the residue was purified by column chromatography on silica gel using a gradient of 0-10% methanol in dichloromethane as eluent to yield the title product, 0.38 mg (70%).

Workup

  1. customThe vial was capped
  2. customevacuated
  3. customflushed with nitrogen
  4. temperaturecooled
  5. filtrationfiltered through a pad of silica gel
  6. washThe pad was eluted with 10% methanol in ethyl acetate
  7. customThe solvents were evaporated
  8. customthe residue was purified by column chromatography on silica gel using a gradient of 0-10% methanol in dichloromethane as eluent

Sources & evidence

ORD record
ord-0894b687d26c4f6693d45598af804204
Source dataset
uspto-grants-2016_09
Patent number
US09439904B2

Reaction notes

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