Ethyl Acetate → 4-[6,7-Bis(methyloxy)quinolin-4-yl]-7-bromo-2,3,4,5-tetrahydro-1,4-benzoxazepine

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Reaktionsgleichung

Cl.[Br:2][C:3]1[CH:4]=[CH:5][C:6]2[O:12][CH2:11][CH2:10][NH:9][CH2:8][C:7]=2[CH:13]=1.Cl[C:15]1[C:24]2[C:19](=[CH:20][C:21]([O:27][CH3:28])=[C:22]([O:25][CH3:26])[CH:23]=2)[N:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN1CCCC1>[CH3:26][O:25][C:22]1[CH:23]=[C:24]2[C:19](=[CH:20][C:21]=1[O:27][CH3:28])[N:18]=[CH:17][CH:16]=[C:15]2[N:9]1[CH2:8][C:7]2[CH:13]=[C:3]([Br:2])[CH:4]=[CH:5][C:6]=2[O:12][CH2:11][CH2:10]1

Komponenten

Reaktionsbedingungen

Temperatur: 160 °C

Versuchsvorschrift

A mixture of 7-bromo-2,3,4,5-tetrahydro-1,4-benzoxazepine hydrochloride (300 mg, 1.13 mmol), 4-chloro-6,7-dimethoxyquinoline (253 mg, 1.13 mmol), and potassium carbonate (470 mg, 3.40 mmol) in N-methylpyrrolidine (2 mL) was stirred at 160° C. for 17 h. Ethyl acetate (75 mL) was added and the mixture was washed with water (3×25 mL) and brine (25 mL), dried over sodium sulfate, and concentrated. Column chromatography on silica (dichloromethane:methanol 95:5) afforded 4-[6,7-bis(methyloxy)quinolin-4-yl]-7-bromo-2,3,4,5-tetrahydro-1,4-benzoxazepine (80 mg). MS (EI) for C20H19BrN2O3: 416 (MH+).

Aufarbeitung

washthe mixture was washed with water (3×25 mL) and brine (25 mL)
dry with materialdried over sodium sulfate
concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag: ord-0f6eff0172b3404281ea183c831fa07d
Quelldatensatz: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08648066B2

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