Reaktion #165380

Reaktionsgleichung

trifluoroacetic acid

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

sodium hydrogencarbonate

thioanisole

→

title compound

Ausbeute 62.4%

4-(3-(2-Amino-5-chloro-pyridin-3-yl)-isoxazol-5-ylmethyl)-phenol

Ausbeute 62.4%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionwhich was extracted with ethyl acetate
2. 2
   SonstigeThe organic layer was separated
3. 3
   Waschenwashed with water and 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 NH silica gel column chromatography (ethyl acetate: methanol=20:1)

Vorschrift

To a trifluoroacetic acid (6 mL) solution of 3-(5-(4-benzyloxy-benzyl)-isoxazol-3-yl)-5-chloro-pyridin-2-ylamine (304 mg, 0.776 mmol) described in Manufacturing Example 29-2-3 was added thioanisole (364 mL, 3.10 mmol) at 0° C., which was stirred for 3 hours at room temperature. To this reaction mixture were added sodium hydrogencarbonate and water at 0° C., which was extracted with ethyl acetate. The organic layer was separated, washed with water and 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 NH silica gel column chromatography (ethyl acetate: methanol=20:1) to obtain the title compound (146 mg, 62%).

Quelle