Cesium carbonate → HCID 68830556, compound

HRID 1986479Notes

Reaction equation

HRID 1986479 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Br[C:48]1[CH:49]=[C:50]2[C:55](=[CH:56][CH:57]=1)[N:54]=[C:53]([CH2:58][CH:59]([CH3:61])[CH3:60])[C:52]([C:62]#[N:63])=[C:51]2[C:64]1[CH:69]=[CH:68][C:67]([CH3:70])=[CH:66][CH:65]=1.[NH:71]1[CH2:76][CH2:75][NH:74][CH2:73][C:72]1=[O:77].C(=O)([O-])[O-].[Cs+].[Cs+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O1CCOCC1>[CH2:58]([C:53]1[C:52]([C:62]#[N:63])=[C:51]([C:64]2[CH:69]=[CH:68][C:67]([CH3:70])=[CH:66][CH:65]=2)[C:50]2[C:55](=[CH:56][CH:57]=[C:48]([N:74]3[CH2:75][CH2:76][NH:71][C:72](=[O:77])[CH2:73]3)[CH:49]=2)[N:54]=1)[CH:59]([CH3:60])[CH3:61]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 231360Piperazin-2-oneHCID 634876Binap, (A+-)-HCID 51050239HCID 51050239, compound

Product 1

HCID 68830556HCID 68830556, compoundYield 71%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
40 °C

Procedure

Palladium acetate (0.014 g, 0.063 mmol) and racemic-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.12 g, 0.19 mmol) were added to 1,4-dioxane (30 ml) under a nitrogen atmosphere, and the mixture was stirred at 40° C. for 30 min. The reaction mixture was cooled to room temperature and 6-bromo-2-isobutyl-4-(4-methylphenyl)quinoline-3-carbonitrile (0.50 g, 1.3 mmol), 2-piperazinone (0.50 ml, 5.0 mmol) and cesium carbonate (0.57 g, 1.8 mmol) were added. The mixture was stirred under a nitrogen atmosphere at 80° C. for 2 days. The reaction mixture was cooled and partitioned between ethyl acetate and water, and the aqueous layer was extracted with ethyl acetate. The organic layer and the extract were combined, washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography to give 2-isobutyl-4-(4-methylphenyl)-6-(3-oxopiperazin-1-yl)quinoline-3-carbonitrile (0.35 g, yield 71%) as a yellow powder.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. stirringThe mixture was stirred under a nitrogen atmosphere at 80° C. for 2 days
  3. temperatureThe reaction mixture was cooled
  4. custompartitioned between ethyl acetate and water
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. washwashed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was evaporated under reduced pressure
  9. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-29f068fb47194ff3ba1fd2bd4240449e
Source dataset
uspto-grants-2009_06
Patent number
US07547710B2

Reaction notes

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