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

HRID 515724

反応式

HRID 515724 の反応式
[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]

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
50 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-6678cdc36b194fd38916c64f6fd58c7d
出典データセット
uspto-grants-2015_08
特許番号
US09108969B2

関連ノート

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