Methanol → 6-Methoxy-3-(methoxymethyl)-2-methyl-4-phenylisoquinolin-1(2H)-one
Reaktionsgleichung
[CH3:1][OH:2].[H-].[Na+].Br[CH2:6][C:7]1[N:8]([CH3:26])[C:9](=[O:25])[C:10]2[C:15]([C:16]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[CH:14][C:13]([O:23][CH3:24])=[CH:12][CH:11]=2>CN(C)C=O>[CH3:24][O:23][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:25])[N:8]([CH3:26])[C:7]([CH2:6][O:2][CH3:1])=[C:16]2[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1Komponenten
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
To a solution of methanol (0.057 mL, 1.40 mmol) in 2 mL of dimethylformamide was added sodium hydride (45 mg, 60% dispersion in mineral oil, 1.11 mmol). After 10 minutes, 3-(bromomethyl)-6-methoxy-2-methyl-4-phenylisoquinolin-1(2H)-one was added (100 mg, 0.279 mmol). After 30 minutes, the reaction mixture was cooled to 0° C., and quenched with 1 mL of saturated NaHCO3 solution. The mixture was partitioned between EtOAc and saturated NaHCO3 solution, and the organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude residue was purified by flash chromatography through SiO2 (50% EtOAc/hexane) to provide the titled product as a white solid. 1H-NMR (500 MHz, CDCl3) δ 8.43 (d, J=9.0 Hz, 1H), 7.44-7.50 (m, 3H), 7.29-7.31 (m, 2H), 6.91 (dd, J=9.0, 2.5 Hz, 1H), 6.42 (d, J=2.5 Hz, 1H), 4.18 (s, 2H), 3.75, (s, 3H), 3.69 (s, 3H), 3.24 (s, 3H) ppm. ESI+ MS: 310.23 [M+H]+.
Aufarbeitung
- waitAfter 30 minutes
- customquenched with 1 mL of saturated NaHCO3 solution
- customThe mixture was partitioned between EtOAc and saturated NaHCO3 solution
- washthe organic layer was washed with brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe crude residue was purified by flash chromatography through SiO2 (50% EtOAc/hexane)
Quellen und Nachweise
- ORD-Eintrag
- ord-71714bbd1b994b68a931cc69b02d834a
- Quelldatensatz
- uspto-grants-2010_05
- Patentnummer
- US07709476B2
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