Cesium carbonate → Ethyl 2-(2-(3,4-Diethoxybenzyloxy)-6,7,8,9-tetrahydropyrido[1,2-a]indol-9-yl)acetate

HRID 515719

반응식

HRID 515719 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.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([O:35][CH2:36][CH3:37])=[C:31]([O:38][CH2:39][CH3:40])[CH:30]=1>CC(N(C)C)=O>[CH2:39]([O:38][C:31]1[CH:30]=[C:29]([CH:34]=[CH:33][C:32]=1[O:35][CH2:36][CH3:37])[CH2:28][O: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)[CH3:40]

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 24348314-Chloromethyl-1,2-diethoxy-benzeneHCID 67249257Ethyl 2-(2-hydroxy-6,7,8,9-tetrahydropyrido[1,2-a]indol-9-yl)acetate

생성물 1

HCID 67250738Ethyl 2-(2-(3,4-Diethoxybenzyloxy)-6,7,8,9-tetrahydropyrido[1,2-a]indol-9-yl)acetate수율 62.3%

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

반응 조건

온도
60 °C

실험 절차

Ethyl 2-(2-hydroxy-6,7,8,9-tetrahydropyrido[1,2-a]indol-9-yl)acetate (0.100 g, 0.366 mmol), cesium carbonate (0.179 g, 0.549 mmol) and 4-(chloromethyl)-1,2-diethoxybenzene (0.118 g, 0.549 mmol) were taken up in DMA (2 mL) and heated to 60° C. for 16 h in a 20 mL sealed scintillation vial. The reaction was cooled down to room temperature and filtered by vacuum filtration through a glass fiber paper. The solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (0.103 g) as an off-white solid. LCMS m/z=452.3 [M+H]+.

후처리

  1. customsealed scintillation vial
  2. temperatureThe reaction was cooled down to room temperature
  3. filtrationfiltered by vacuum filtration through a glass fiber paper
  4. customThe solvent was removed under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-07604347832640e4b3e153d96953c959
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09108969B2

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