4-Chloro-6,7-dimethoxyquinoline → 4-Benzoyl-1-(4-(6,7-dimethoxyquinolin-4-yloxy)-3 fluorophenyl)pyrrolidin-2-one

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Reaktionsgleichung

Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[C:16]([CH:24]1[CH2:28][N:27]([C:29]2[CH:34]=[CH:33][C:32]([OH:35])=[C:31]([F:36])[CH:30]=2)[C:26](=[O:37])[CH2:25]1)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C1C=CN=CC=1)C.O1CCOCC1.CCOC(C)=O>[C:16]([CH:24]1[CH2:28][N:27]([C:29]2[CH:34]=[CH:33][C:32]([O:35][C:2]3[C:11]4[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=4)[N:5]=[CH:4][CH:3]=3)=[C:31]([F:36])[CH:30]=2)[C:26](=[O:37])[CH2:25]1)(=[O:23])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Komponenten

Reaktionsbedingungen

Temperatur: 160 °C

Versuchsvorschrift

A mixture of 4-chloro-6,7-dimethoxyquinoline (0.38 g, 1.67 mmol), 4-benzoyl-1-(3-fluoro-4-hydroxyphenyl)pyrrolidin-2-one (Step 3, 0.40 g, 1.67 mmol) and DMAP (0.204 g, 1.67 mmol) in 4 mL of dioxane (in a microwave tube) was heated in a microwave (Personal Chemistry, Emrys Optimizer) at 160° C. for 1 h. The mixture was cooled to RT and diluted with 50 mL of EtOAc. The solution was washed with 20 mL of satd. NaHCO3 followed by 20 mL of brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by chromatography (50% to 100% EtOAc in hexanes then to 5% MeOH/EtOAc) to provide a white solid. MS (ESI pos. ion) m/z: 487.4 (M+H). Calc'd Exact Mass for C28H23FN2O5: 486.49.

Aufarbeitung

temperatureThe mixture was cooled to RT
washThe solution was washed with 20 mL of satd
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
customThe residue was purified by chromatography (50% to 100% EtOAc in hexanes
customto 5% MeOH/EtOAc) to provide a white solid

Quellen und Nachweise

ORD-Eintrag: ord-61631bea82a142edb4401d120490eb7d
Quelldatensatz: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07652009B2

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