2-Mercaptoethanol → 3-{[(2-Hydroxyethyl)thio]methyl}-6-methoxy-2-methyl-4-phenylisoquinolin-1(2H)-one

HRID 2233053Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2233053
Br[CH2:2][C:3]1[N:4]([CH3:22])[C:5](=[O:21])[C:6]2[C:11]([C:12]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[CH:10][C:9]([O:19][CH3:20])=[CH:8][CH:7]=2.[OH:23][CH2:24][CH2:25][SH:26].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[OH:23][CH2:24][CH2:25][S:26][CH2:2][C:3]1[N:4]([CH3:22])[C:5](=[O:21])[C:6]2[C:11]([C:12]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[CH:10][C:9]([O:19][CH3:20])=[CH:8][CH:7]=2

Komponenten

5

Edukt 3

HCID 15672-MercaptoethanolHCID 10796Cesium carbonateHCID 225559473-(bromomethyl)-6-methoxy-2-methyl-4-phenylisoquinolin-1(2H)-one

Produkt 1

HCID 113826983-{[(2-Hydroxyethyl)thio]methyl}-6-methoxy-2-methyl-4-phenylisoquinolin-1(2H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 3-(bromomethyl)-6-methoxy-2-methyl-4-phenylisoquinolin-1(2H)-one (125 mg, 0.349 mmol) in 5 mL of dimethylformamide was added 2-hydroxyethanethiol (0.027 mL, 0.38 mmol) and cesium carbonate (227 mg, 0.698 mmol). After one hour, the reaction mixture was partitioned between EtOAc and water, and the organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude residue was purified by recrystallization from EtOAc/hexane to provide the titled product. 1H-NMR (500 MHz, CDCl3) δ 8.41 (d, J=9.0 Hz, 1H), 7.45-7.54 (m, 3H), 7.34-7.36 (m, 2H), 7.04 (dd, J=9.0, 2.5 Hz, 1H), 6.35 (d, J=2.5 Hz, 1H), 3.83, (s, 3H), 3.68 (s, 3H), 3.63 (s, 2H), 3.41 (m, 2H), 2.58 (t, J=5.6 Hz, 2H) ppm. ESI+ MS: 356.14 [M+H]+.

Aufarbeitung

  1. customthe reaction mixture was partitioned between EtOAc and water
  2. washthe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified by recrystallization from EtOAc/hexane

Quellen und Nachweise

ORD-Eintrag
ord-06a6014d45a14898b4a339fe21433c65
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07709476B2

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