تفاعل #165380

معادلة التفاعل

trifluoroacetic acid

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

sodium hydrogencarbonate

thioanisole

→

title compound

المردود 62.4%

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

المردود 62.4%

المذيبات

water

ظروف التفاعل

المعالجة

1. 1
   استخلاصwhich was extracted with ethyl acetate
2. 2
   أخرىThe organic layer was separated
3. 3
   غسيلwashed with water and saturated aqueous sodium chloride
4. 4
   تجفيفdried over anhydrous magnesium sulfate
5. 5
   ترشيحfiltered
6. 6
   تركيزThe filtrate was concentrated under a reduced pressure
7. 7
   أخرىthe residue was purified by NH silica gel column chromatography (ethyl acetate: methanol=20:1)

الإجراء التجريبي

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%).

المصدر