5-Benzyloxy-2-fluoro-4-methylphenol → 4-(5-Benzyloxy-2-fluoro-4-methylphenoxy)-6-methoxy-7-(3-morpholinopropoxy)quinoline

HRID 393600

Reaktionsgleichung

Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[CH2:24]([O:31][C:32]1[C:33]([CH3:40])=[CH:34][C:35]([F:39])=[C:36]([OH:38])[CH:37]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.CC(C)([O-])C.[K+]>CS(C)=O>[CH2:24]([O:31][C:32]1[C:33]([CH3:40])=[CH:34][C:35]([F:39])=[C:36]([CH:37]=1)[O:38][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Komponenten

Reaktionsbedingungen

Temperatur: 160 °C

Versuchsvorschrift

4-Chloro-6-methoxy-7-(3-morpholinopropoxy)quinoline (250 mg, 0.74 mmol) was added to a solution of 5-benzyloxy-2-fluoro-4-methylphenol (257 mg 1.1 mmol) and potassium t-butoxide (125 mg, 1.1 mmol) in DMSO (3 ml) and the mixture heated at 160° C. for 1.5 hours. The mixture was allowed to cool and was partitioned between water and ethyl acetate. The organic layer was separated, washed with brine, dried (MgSO4), and the solvent removed by evaporation. The residue was purified by column chromatography eluting with methylene chloride/methanol (95/5) to give 4-(5-benzyloxy-2-fluoro-4-methylphenoxy)-6-methoxy-7-(3-morpholinopropoxy)quinoline (105 mg, 69%).

Aufarbeitung

temperatureto cool
customwas partitioned between water and ethyl acetate
customThe organic layer was separated
washwashed with brine
dry with materialdried (MgSO4)
customthe solvent removed by evaporation
customThe residue was purified by column chromatography
washeluting with methylene chloride/methanol (95/5)

Quellen und Nachweise

ORD-Eintrag: ord-5a38eee06c30427a9e107d76bcd0c311
Quelldatensatz: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06809097B1

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