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

HRID 75480
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HRID 75480 반응식
[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
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참가 물질

8

반응물 4

HCID 8028TetrahydrofuranHCID 10796Cesium carbonateHCID 36600898-Quinolinyl trifluoromethanesulfonate2회HCID 226363811-Tert-butyl-4-piperazine carboxylate2회

생성물 1

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

시약·촉매·용매 3

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

실험 절차

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.

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-aedb96e59e354a708b31212b81df7a88
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08835436B2

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