Cesium carbonate → HCID 89825709, compound

HRID 631799Notes

Reaction equation

HRID 631799 reaction equation
C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:54]1[CH:63]=[CH:62][C:61]2[C:56](=[CH:57][CH:58]=[CH:59][CH:60]=2)[N:55]=1.[NH2:64][CH2:65][CH2:66][NH:67][C:68](=[O:74])[O:69][C:70]([CH3:73])([CH3:72])[CH3:71]>O1CCOCC1.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[N:55]1[C:56]2[C:61](=[CH:60][CH:59]=[CH:58][CH:57]=2)[CH:62]=[CH:63][C:54]=1[NH:64][CH2:65][CH2:66][NH:67][C:68](=[O:74])[O:69][C:70]([CH3:72])([CH3:71])[CH3:73]

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 119282-ChloroquinolineHCID 187201N-BOC-ethylenediamineHCID 634876Binap, (A+-)-

Product 1

HCID 89825709HCID 89825709, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

Palladium acetate (63 mg, 0.28 mmol), BINAP (250 mg, 0.4 mmol) and cesium carbonate (1.3 g, 4 mmol) were suspended in anhydrous 1,4-dioxane (9 ml) under an argon atmosphere and sonicated for 40 minutes. 2-Chloroquinoline (343 mg, 2 mmol) and tert-butyl N-(2-aminoethyl)carbamate (320 mg, 2 mmol) were added and the resulting mixture was stirred at 110° C. for three hours. The reaction mixture was diluted with ethyl acetate, the resulting precipitate was removed by centrifugation and decantation. The supernatant was evaporated to dryness under reduced pressure. The residue was dissolved in DCM, filtered through a short silica column; the product was eluted with a 1-to-1 mixture of DCM and diethylether. After evaporation of the solvent under reduced pressure 137 mg of a solid were obtained (0.44 mmol, 22%). MS(ESI) m/z=288.2 [M+1]+.

Workup

  1. customsonicated for 40 minutes
  2. customthe resulting precipitate was removed by centrifugation and decantation
  3. customThe supernatant was evaporated to dryness under reduced pressure
  4. dissolutionThe residue was dissolved in DCM
  5. filtrationfiltered through a short silica column
  6. washthe product was eluted with a 1-to-1 mixture of DCM and diethylether
  7. customAfter evaporation of the solvent under reduced pressure 137 mg of a solid
  8. customwere obtained (0.44 mmol, 22%)

Sources & evidence

ORD record
ord-39a04c848ca8416893cef5a43b901ec3
Source dataset
uspto-grants-2016_04
Patent number
US09321724B2

Reaction notes

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