Diisopropylethylamine → 6-bromo-N-(4-((dimethylamino)methyl)phenyl)-3-(methylsulfonyl)quinolin-4-amine

HRID 2271561Notizen

Reaktionsgleichung

[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([S:12]([CH3:15])(=[O:14])=[O:13])=[C:5]2Cl.[CH3:17][N:18]([CH2:20][CH:21]1[CH2:26][CH2:25][CH:24]([NH2:27])[CH2:23][CH2:22]1)[CH3:19].C(N(CC)C(C)C)(C)C>O1CCOCC1.C(=O)(O)[O-].[Na+]>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([S:12]([CH3:15])(=[O:14])=[O:13])=[C:5]2[NH:27][C:24]1[CH:23]=[CH:22][C:21]([CH2:20][N:18]([CH3:19])[CH3:17])=[CH:26][CH:25]=1

Komponenten

Reaktionsbedingungen

Temperatur: 90 °C

Versuchsvorschrift

To a suspension of 6-bromo-4-chloro-3-(methylsulfonyl)quinoline (250 mg, 0.78 mmol) in dioxane (8 mL) was added 4-((dimethylamino)methyl)cyclohexanamine (233 mg, 1.55 mmol) and N,N-diisopropylethylamine (0.42 mL, 2.4 mmol). The reaction mixture was heated at 90° C. for 4 h. The reaction mixture was cooled to room temperature, diluted with saturated sodium bicarbonate solution and extracted with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and concentrated. Purification by column chromatography (silica, 0-20% methanol/dichloromethane) afforded the desired product (225 mg, 66%) as a yellow solid. ESI MS m/z 434 [C29H20BrN3O2+H]+

Aufarbeitung

temperatureThe reaction mixture was cooled to room temperature
extractionextracted with ethyl acetate
dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
concentrationconcentrated
customPurification by column chromatography (silica, 0-20% methanol/dichloromethane)

Quellen und Nachweise

ORD-Eintrag: ord-2b884746482b414ea05680b14a6f2296
Quelldatensatz: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09120749B2

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