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Water → HCID 66819254, Verbindung

HRID 2045963
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2045963
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[NH:4][C:3]=1[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=1.[C:21]([O:25][C:26](=[O:31])[NH:27][CH2:28][CH2:29]Br)([CH3:24])([CH3:23])[CH3:22].C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C)C(=O)C>[C:21]([O:25][C:26](=[O:31])[NH:27][CH2:28][CH2:29][O:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[NH:4][C:3]=1[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=1)([CH3:24])([CH3:23])[CH3:22]
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Komponenten

6

Edukt 4

HCID 962WaterHCID 10796Cesium carbonateHCID 4103526tert-Butyl N-(2-bromoethyl)carbamateHCID 44315704HCID 44315704, Verbindung

Produkt 1

HCID 66819254HCID 66819254, VerbindungAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374
Dimethylacetamide
Lösungsmittel

Versuchsvorschrift

To a solution of 3.79 g (14.19 mmol) of 4-hydroxy-3-(3-methoxy-phenyl)-2H-isoquinolin-1-one in N,N-dimethylacetamide (90 mL), 3.18 g (14.19 mmol) of (2-bromo-ethyl)-carbamic acid tert-butyl ester and 5.09 g (15.6 mmol) of cesium carbonate were added and the resulting mixture was stirred at room temperature for 2 hours under argon. Water was added to the reaction mixture and this was extracted twice with ethyl acetate. The combined organic layers were washed at least three times with water and then evaporated to dryness. The crude was purified by flash chromatography (eluant: ethyl acetate/hexane 1/1) to afford 3.2 g of the title compound (55%).

Aufarbeitung

  1. extractionthis was extracted twice with ethyl acetate
  2. washThe combined organic layers were washed at least three times with water
  3. customevaporated to dryness
  4. customThe crude was purified by flash chromatography (eluant: ethyl acetate/hexane 1/1)

Quellen und Nachweise

ORD-Eintrag
ord-f416acc489834c3f9329587a92aed658
Quelldatensatz
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08592416B2

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