Dimethylformamide → Ethyl 2-(2-(4-Isopropoxy-3-(trifluoromethyl)benzyloxy)-6,7,8,9-tetrahydropyrido[1,2-a]indol-9-yl)acetate

HRID 515724

반응식

HRID 515724 반응식
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]1[CH2:11][CH2:12][CH2:13][CH:14]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:6]1=[CH:5]2.CN(C=O)C.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:33][C:34]1[CH:39]=[CH:38][C:37]([O:40][CH:41]([CH3:43])[CH3:42])=[C:36]([C:44]([F:47])([F:46])[F:45])[CH:35]=1>CCOC(C)=O.O>[CH:41]([O:40][C:37]1[CH:38]=[CH:39][C:34]([CH2:33][O:1][C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[N:7]2[CH2:11][CH2:12][CH2:13][CH:14]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:6]2=[CH:5]3)=[CH:35][C:36]=1[C:44]([F:45])([F:46])[F:47])([CH3:43])[CH3:42]

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 533782354-(Chloromethyl)-1-isopropoxy-2-(trifluoromethyl)benzeneHCID 67249257Ethyl 2-(2-hydroxy-6,7,8,9-tetrahydropyrido[1,2-a]indol-9-yl)acetate

생성물 1

HCID 67248678Ethyl 2-(2-(4-Isopropoxy-3-(trifluoromethyl)benzyloxy)-6,7,8,9-tetrahydropyrido[1,2-a]indol-9-yl)acetate수율 80.5%

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

반응 조건

온도
50 °C

실험 절차

Ethyl 2-(2-hydroxy-6,7,8,9-tetrahydropyrido[1,2-a]indol-9-yl)acetate (0.107 g, 0.391 mmol) was dissolved in anhydrous DMF (3.91 mL, 0.391 mmol). Cesium carbonate (0.166 g, 0.509 mmol) was added followed by 4-(chloromethyl)-1-isopropoxy-2-(trifluoromethyl)benzene (0.122 mL, 0.587 mmol) to give a suspension. The reaction was heated at 50° C. for 5 h. The solvent was evaporated in vacuo to give a residue which was dissolved in EtOAc (50 mL) and water (20 mL). The organic layer was washed with water (20 mL), brine (20 mL), and dried over MgSO4. The solvent was evaporated in vacuo to give an oil which was purified by silica gel column chromatography to give the title compound as an oil (0.154 g). LCMS m/z=490.4 [M+H]+; 1H NMR (400 MHz, Acetonitrile-d3) α ppm 1.24 (t, J=7.14 Hz, 3H), 1.32 (d, J=6.06 Hz, 6H), 1.50-1.64 (m, 1H), 2.1 (m, 3H), 2.55 (dd, J=15.73, 8.02 Hz, 1H), 2.86 (dd, J=15.66, 5.94 Hz, 1H), 3.33-3.47 (m, 1H), 3.79-3.88 (m, 1H), 4.06-4.21 (m, 3H), 4.74 (dt, J=12.09, 6.02 Hz, 1H), 5.04 (s, 2H), 6.13 (s, 1H), 6.81 (dd, J=8.78, 2.46 Hz, 1H), 7.04 (d, J=2.40 Hz, 1H), 7.16 (d, J=8.59 Hz, 1H), 7.19 (d, J=8.84 Hz, 1H), 7.62 (d, J=8.59 Hz, 1H), 7.66 (d, J=1.89 Hz, 1H).

후처리

  1. customto give a suspension
  2. customThe solvent was evaporated in vacuo
  3. customto give a residue which
  4. washThe organic layer was washed with water (20 mL), brine (20 mL)
  5. dry with materialdried over MgSO4
  6. customThe solvent was evaporated in vacuo
  7. customto give an oil which
  8. customwas purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-6678cdc36b194fd38916c64f6fd58c7d
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09108969B2

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