Reaktion #165367

Reaktionsgleichung

trifluoroacetic acid

5-(3-(4-benzyloxy-benzyl)-isoxazol-5-yl)-pyridin-2-ylamine

Sodium hydrogencarbonate

thioanisole

→

title compound

Ausbeute 74.3%

4-(5-(6-Amino-pyridin-3-yl)-isoxazol-3-ylmethyl)-phenol

Ausbeute 74.3%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionwhich was extracted with ethyl acetate
2. 2
   SonstigeThe organic layer was separated
3. 3
   Waschenwashed with saturated aqueous sodium chloride
4. 4
   Trocknendried over anhydrous magnesium sulfate
5. 5
   Filtrationfiltered
6. 6
   EinengenThe filtrate was concentrated under a reduced pressure
7. 7
   Sonstigethe residue was purified by silica gel column chromatography (ethyl acetate: methanol=10:1)

Vorschrift

To a trifluoroacetic acid (5 mL) solution of 5-(3-(4-benzyloxy-benzyl)-isoxazol-5-yl)-pyridin-2-ylamine (270 mg, 0.755 mmol) described in Example 28 was added thioanisole (355 μL, 3.02 mmol) at 0° C., which was stirred for 1 hour and 20 minutes at room temperature. Sodium hydrogencarbonate and water were added to the reaction mixture at 0° C., which was extracted with ethyl acetate. The organic layer was separated, washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate: methanol=10:1) to obtain the title compound (150 mg, 74%).

Quelle