Cesium carbonate → 8-(4-t-Butyloxycarbonylpiperazin-1-yl)quinoline

HRID 339734Notes

Reaction equation

HRID 339734 reaction equation
[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.FC(F)(F)S(O[C:20]1[CH:21]=[CH:22][CH:23]=[C:24]2[C:29]=1[N:28]=[CH:27][CH:26]=[CH:25]2)(=O)=O.C([O-])([O-])=O.[Cs+].[Cs+]>C1COCC1.CCOCC.CC([O-])=O.CC([O-])=O.[Pd+2].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>[N:28]1[C:29]2[C:24](=[CH:23][CH:22]=[CH:21][C:20]=2[N:4]2[CH2:5][CH2:6][N:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2][CH2:3]2)[CH:25]=[CH:26][CH:27]=1

Participants

8

Reactant 3

HCID 10796Cesium carbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 36600898-Quinolinyl trifluoromethanesulfonate

Product 1

HCID 155406788-(4-t-Butyloxycarbonylpiperazin-1-yl)quinolineYield 74.9%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 634876Binap, (A+-)-CatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

t-Butyl piperazine-1-carboxylate (8.6 g, 46 mmol) and quinolin-8-yl trifluoromethanesulfonate (11 g, 39.6 mmol) were added to a solution of Cs2CO3 (18 g, 55 mmol), BINAP (1.07 g) and Pd(OAc)2 (367 mg) in THF (100 ml). The reaction mixture was refluxed for 1 day and then cooled down to room temperature. The resulting solution was diluted with Et2O (100 ml) and then filtered with Celite. The organic solution was evaporated under reduced pressure, and the residue was purified with normal preparative column to give rise to desired compound (9.3 g, 74% yield) as light yellow solid.

Workup

  1. temperatureThe reaction mixture was refluxed for 1 day
  2. filtrationfiltered with Celite
  3. customThe organic solution was evaporated under reduced pressure
  4. customthe residue was purified with normal preparative column

Sources & evidence

ORD record
ord-b5efeb08621741949fdae58834bc93a9
Source dataset
uspto-grants-2014_11
Patent number
US08895558B2

Reaction notes

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