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

HRID 339734
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HRID 339734 반응식
[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
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참가 물질

8

반응물 3

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

생성물 1

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

시약·촉매·용매 4

HCID 167845palladium(II) acetate촉매
HCID 634876
Binap, (A+-)-
촉매
HCID 3283Diethyl Ether용매
HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b5efeb08621741949fdae58834bc93a9
출처 데이터셋
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08895558B2

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