Cesium carbonate → Tert-butyl 4-(2-methylquinolin-5-yl)piperazine-1-carboxylate

HRID 15768

반응식

HRID 15768 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.C(=O)([O-])[O-].[Cs+].[Cs+].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.FC(F)(F)S(O[C:72]1[CH:81]=[CH:80][CH:79]=[C:78]2[C:73]=1[CH:74]=[CH:75][C:76]([CH3:82])=[N:77]2)(=O)=O>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:82][C:76]1[CH:75]=[CH:74][C:73]2[C:78](=[CH:79][CH:80]=[CH:81][C:72]=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)[N:77]=1

참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 634876Binap, (A+-)-HCID 498518992-Methylquinolin-5-yl trifluoromethanesulfonate

생성물 1

HCID 49851900Tert-butyl 4-(2-methylquinolin-5-yl)piperazine-1-carboxylate수율 62%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 1140Toluene용매

실험 절차

tert-Butyl 1-piperazine carboxylate (1.6 g; 1.2 eq), cesium carbonate (1.7 g; 1.5 eq), palladium acetate (0.33 g; 0.14 eq) and 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.97 mg; 0.15 eq) were added to a solution of 2-methyl-5-quinolinyl trifluoromethanesulfonate (D1) in toluene (20 mL) under an inert atmosphere. The reaction mixture was stirred at reflux under nitrogen for 8 hours. The reaction was quenched at room temperature using a saturated aqueous solution of ammonium chloride (15 mL) and extracted into ethyl acetate (3×20 mL). The organic layers were combined, dried over Na2SO4 and concentrated under reduced pressure. The crude was purified by flash chromatography, eluting with ethyl acetate/cyclohexane (3/7) affording the title compound in 62% yield (1.4 g).

후처리

  1. temperatureat reflux under nitrogen for 8 hours
  2. customThe reaction was quenched at room temperature
  3. extractionextracted into ethyl acetate (3×20 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe crude was purified by flash chromatography
  7. washeluting with ethyl acetate/cyclohexane (3/7)

출처 및 근거

ORD 기록
ord-8a5315f9c363403ea8321f3dfc2a3dea
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732600B2

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