Cesium carbonate → 77-LH-28-1

HRID 1986812노트

반응식

HRID 1986812 반응식
CO[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[CH2:7][CH2:6]2.Cl[CH2:15][CH2:16][CH2:17]I.C([O-])([O-])=O.[Cs+].[Cs+].C([O-])([O-])=O.[K+].[K+].[CH2:31]([CH:35]1[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1)[CH2:32][CH2:33][CH3:34]>C(#N)C.O>[CH2:31]([CH:35]1[CH2:40][CH2:39][N:38]([CH2:15][CH2:16][CH2:17][N:9]2[C:10]3[C:5](=[CH:4][CH:3]=[CH:12][CH:11]=3)[CH2:6][CH2:7][C:8]2=[O:13])[CH2:37][CH2:36]1)[CH2:32][CH2:33][CH3:34]

참가 물질

8

반응물 5

HCID 10796Cesium carbonateHCID 11430Potassium CarbonateHCID 813631-Chloro-3-iodopropaneHCID 108884676-Methoxy-1,2,3,4-tetrahydroquinolin-2-oneHCID 132838674-Butylpiperidine

생성물 1

HCID 1023675877-LH-28-1

시약·촉매·용매 2

HCID 962Water용매2회HCID 6342Acetonitrile용매

실험 절차

6-Methoxy-3,4-dihydro-1H-quinolin-2-one (108 mg, 0.61 mmol), 1-chloro-3-iodopropane (64 μl, 0.6 mmol) and Cs2CO3 (290 mg, 0.9 mmol) in acetonitrile (2 mL) were shaken at 60° C. for 14 h then the reaction was cooled to room temperature. Water (5 mL) was added and the product was extracted with ethyl acetate (2×10 mL). The organic layer was dried (Na2SO4), filtered and concentrated in vacuo. The syrup was dissolved in acetonitrile (4 mL). KI (83 mg, 3.6 mmol), K2CO3 (100 mg, 0.6 mmol) and 4-butylpiperidine (83 μl, 0.5 mmol) were added and the reaction mixture was shaken at 60° C. for 16 h. Water (5 mL) was added and the product was extracted with ethyl acetate (2×10 mL). The organic layer was dried (Na2SO4) and concentrated in vacuo. The product was purified by column chromatography (eluent: 20% methanol in ethyl acetate) to yield the title compound. Yield: 24.8 mg, 11.3%. HPLC-MS: M+1+=359.5 (UV/MS (%)=90/78). 1H NMR (400 MHz, CDCl3): δ=0.89 (3H, t), 1.12-1.34 (9H, m), 1.67 (2H, broad d), 1.85 (2H, quin.), 1.93 (2H, broad t), 2.39 (2H, t), 2.59 (2H, dd), 2.83 (2H, t), 2.90 (2H, broad d), 3.76 (3H, s), 3.94 (2H, t), 6.70 (1H, d), 6.74 (1H, dd), 7.01 (1H, d). 13C NMR (CDCl3): d 14.3, 23.0, 25.0, 26.1, 29.2, 32.1, 32.5 (2C), 35.9, 36.4, 40.8, 54.3 (2C), 55.8, 56.3, 112.2, 114.2, 116.2, 128.3, 133.4, 155.4, 169.9

후처리

  1. extractionthe product was extracted with ethyl acetate (2×10 mL)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. dissolutionThe syrup was dissolved in acetonitrile (4 mL)
  6. extractionthe product was extracted with ethyl acetate (2×10 mL)
  7. dry with materialThe organic layer was dried (Na2SO4)
  8. concentrationconcentrated in vacuo
  9. customThe product was purified by column chromatography (eluent: 20% methanol in ethyl acetate)

출처 및 근거

ORD 기록
ord-95bef6f8a4a44f1e9469d7129239d614
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07550459B2

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