Water → tert-Butyl 2-(7-(3-cyano-4-isopropoxybenzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate

HRID 515717

반응식

HRID 515717 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:31]=[CH:32][C:33]([O:38][CH:39]([CH3:41])[CH3:40])=[C:34]([CH:37]=1)[C:35]#[N:36].O>CN(C=O)C>[C:35]([C:34]1[CH:37]=[C:30]([CH:31]=[CH:32][C:33]=1[O:38][CH:39]([CH3:41])[CH3:40])[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)#[N:36]

참가 물질

6

반응물 4

HCID 962WaterHCID 10796Cesium carbonateHCID 668477035-(Chloromethyl)-2-(propan-2-yloxy)benzonitrileHCID 67249455tert-butyl 2-(7-hydroxy-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate

생성물 1

HCID 67252091tert-Butyl 2-(7-(3-cyano-4-isopropoxybenzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate수율 65.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
60 °C

실험 절차

tert-Butyl 2-(7-hydroxy-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate (0.287 g, 1.000 mmol), cesium carbonate (0.489 g, 1.500 mmol) and 5-(chloromethyl)-2-isopropoxybenzonitrile (0.315 g, 1.500 mmol) were taken up in DMF (2.0 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 poured into water and extracted into ether (2×5 mL). The organic layers were combined and washed with water (3×5 mL), saturated NaCl (1×5 mL), dried over MgSO4, 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 (0.301 g) as a light yellow solid. LCMS m/z=461.5 [M+H]+.

후처리

  1. customsealed scintillation vial
  2. temperatureThe reaction was cooled down to room temperature
  3. extractionextracted into ether (2×5 mL)
  4. washwashed with water (3×5 mL), saturated NaCl (1×5 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered by vacuum filtration through a glass fiber paper
  7. customThe solvent was removed under reduced pressure
  8. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-4a9248a214f54ba6b5ad885becd15ab9
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09108969B2

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