Reaktion #156266

Reaktionsgleichung

sodium iodide

6-Bromo-2-chloro-3-(chloromethyl)quinoline

6-(trifluoromethyl)-4-pyrimidinol

DIEA

→

6-bromo-2-chloro-3-((6-(trifluoromethyl)pyrimidin-4-yloxy)methyl)quinoline

Lösungsmittel

water

CAN

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction was cooled
2. 2
   Extraktionextracted with EtOAc (200 mL)
3. 3
   TrocknenAfter drying with magnesium sulfate the
4. 4
   Sonstigeorganic was evaporated to dryness under reduced pressure
5. 5
   SonstigePurification

Vorschrift

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).

Quelle