반응 #165380

반응 방정식

trifluoroacetic acid

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

sodium hydrogencarbonate

thioanisole

→

title compound

수율 62.4%

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

수율 62.4%

용매

water

반응 조건

후처리

1. 1
   추출which was extracted with ethyl acetate
2. 2
   기타The organic layer was separated
3. 3
   세척washed with water and saturated aqueous sodium chloride
4. 4
   건조dried over anhydrous magnesium sulfate
5. 5
   여과filtered
6. 6
   농축The filtrate was concentrated under a reduced pressure
7. 7
   기타the residue was purified by NH silica gel column chromatography (ethyl acetate: methanol=20:1)

실험 절차

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%).

출처