Sodium Iodide → HCID 86675785, Verbindung

HRID 69084

Reaktionsgleichung

[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([Cl:12])[C:6]([CH2:13]Cl)=[CH:5]2.[F:15][C:16]([F:25])([F:24])[C:17]1[N:22]=[CH:21][N:20]=[C:19]([OH:23])[CH:18]=1.CCN(C(C)C)C(C)C.[I-].[Na+]>O=[N+]([O-])[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[Ce+4].[NH4+].[NH4+].O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([Cl:12])[C:6]([CH2:13][O:23][C:19]1[CH:18]=[C:17]([C:16]([F:25])([F:15])[F:24])[N:22]=[CH:21][N:20]=1)=[CH:5]2

Komponenten

Reaktionsbedingungen

Temperatur: 70 °C

Versuchsvorschrift

6-Bromo-2-chloro-3-(chloromethyl)quinoline (0.60 g, 2.1 mmol), 6-(trifluoromethyl)-4-pyrimidinol (0.34 g, 2.1 mmol), DIEA (0.54 ml, 3.1 mmol) and sodium iodide (0.31 g, 2.1 mmol) were suspended in CAN (50 mL) and heated to 70° C. for 1 h. The reaction was cooled, diluted with water (100 mL) and extracted with EtOAc (200 mL). After drying with magnesium sulfate the organic was evaporated to dryness under reduced pressure. Purification using low pressure silica chromatography (0-10% methanol in DCM gradient) to give the desired 6-bromo-2-chloro-3-((6-(trifluoromethyl)pyrimidin-4-yloxy)methyl)quinoline. Step 2 and 3: The product from step 1 was taken through a procedure similar to that described in steps 3 and 4 of Example 9, to provide the titled compound, o-tolyl-3-((6-(trifluoromethyl)pyrimidin-4-yloxy)methyl)quinolin-2-amine. (ESI, pos. ion) m/z: 411 (M+1).

Aufarbeitung

temperatureThe reaction was cooled
extractionextracted with EtOAc (200 mL)
dry with materialAfter drying with magnesium sulfate the
customorganic was evaporated to dryness under reduced pressure
customPurification

Quellen und Nachweise

ORD-Eintrag: ord-2ba94ad31aea429aaca5434b4d9dc5cd
Quelldatensatz: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08822485B2

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