Methyl iodide → 1-Bromo-4-methoxy-8-phenoxy-isoquinoline-3-carboxylic acid methyl ester

HRID 706216Notizen

Reaktionsgleichung

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

Komponenten

Reaktionsbedingungen

Temperatur: 45 °C

Versuchsvorschrift

A mixture of 1-bromo-4-hydroxy-8-phenoxy-isoquinoline-3-carboxylic acid methyl ester (1.89 g, 5.07 mmol), iodomethane (632 μL, 10.13 mmol), cesium carbonate (3.3 g, 10.13 mmol) and dimethylformamide (15 mL) was stirred at 45° C. for sixteen hours before it was quenched with water, extracted with ethyl acetate. The organic layer was washed with water, brine, dried over sodium sulfate, concentrated in vacuo and the residue was purified by flash column chromatography on silica gel with a gradient of ethyl acetate and hexanes to give the title compound as a yellow solid (1.03 g): MS: (+) m/z 387.64, 389.75 (M+1, 79Br/81Br).

Aufarbeitung

customwas quenched with water
extractionextracted with ethyl acetate
washThe organic layer was washed with water, brine
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo
customthe residue was purified by flash column chromatography on silica gel with a gradient of ethyl acetate and hexanes

Quellen und Nachweise

ORD-Eintrag: ord-10cd0ffde8ee4ffea4cf5014ef22d1c6
Quelldatensatz: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09174976B2

Notizen zur Reaktion

Wird geladen…