Tetrahydrofuran → 8-(4-t-Butyloxycarbonylpiperazin-1-yl)quinoline

HRID 75480Notes

Reaction equation

HRID 75480 reaction equation
[C:1]([N:5]1[CH2:10][CH2:9][N:8]([C:11]([O-:13])=[O:12])[CH2:7][CH2:6]1)([CH3:4])([CH3:3])C.FC(F)(F)S(OC1C=[CH:22][CH:23]=[C:24]2C=1[N:28]=[CH:27][CH:26]=[CH:25]2)(=O)=O.[C:32]([O-])([O-])=O.[Cs+].[Cs+].[CH2:38]1[CH2:42]OC[CH2:39]1>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:3]2[C:24](=[CH:23][CH:22]=[CH:4][C:1]=2[N:5]2[CH2:6][CH2:7][N:8]([C:11]([O:13][C:38]([CH3:39])([CH3:42])[CH3:32])=[O:12])[CH2:9][CH2:10]2)[CH:25]=[CH:26][CH:27]=1

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 10796Cesium carbonateHCID 36600898-Quinolinyl trifluoromethanesulfonate2×HCID 226363811-Tert-butyl-4-piperazine carboxylate2×

Product 1

HCID 155406788-(4-t-Butyloxycarbonylpiperazin-1-yl)quinolineYield 74%

Reagents, catalysts & solvents 3

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

Procedure

t-butyl piperazine-1-carboxylate (compound 31, 8.6 g, 46 mmol) and quinolin-8-yl trifluoromethanesulfonate (compound 30, 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, the residue was purified with normal preparative column to give rise to desired compound (9.3 g, 74% yield) as a 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-aedb96e59e354a708b31212b81df7a88
Source dataset
uspto-grants-2014_09
Patent number
US08835436B2

Reaction notes

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