Cesium carbonate → tert-Butyl 2-(7-(3,4-Diethoxybenzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate

HRID 515725

반응식

HRID 515725 반응식
[OH:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]3[CH2:11][CH2:12][CH:13]([CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:6]3=[CH:5][C:4]=2[CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:29][C:30]1[CH:35]=[CH:34][C:33]([O:36][CH2:37][CH3:38])=[C:32]([O:39][CH2:40][CH3:41])[CH:31]=1>CC(N(C)C)=O>[CH2:40]([O:39][C:32]1[CH:31]=[C:30]([CH:35]=[CH:34][C:33]=1[O:36][CH2:37][CH3:38])[CH2:29][O:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]3[CH2:11][CH2:12][CH:13]([CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:6]3=[CH:5][C:4]=2[CH:3]=1)[CH3:41]

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 24348314-Chloromethyl-1,2-diethoxy-benzeneHCID 67249455tert-butyl 2-(7-hydroxy-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate

생성물 1

HCID 86654874tert-Butyl 2-(7-(3,4-Diethoxybenzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate수율 71.2%

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

반응 조건

온도
60 °C

실험 절차

tert-Butyl 2-(7-hydroxy-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate (0.150 g, 0.522 mmol), cesium carbonate (0.255 g, 0.783 mmol) and 4-(chloromethyl)-1,2-diethoxybenzene (0.168 g, 0.783 mmol) were taken up in DMA (2 mL) and heated to 60° C. for 16 h in a 20 mL sealed scintillation vial. The mixture 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 (173.1 mg).

후처리

  1. customsealed scintillation vial
  2. temperatureThe mixture 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-4c88de49d16045088500dc19d5f4682a
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09108969B2

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