反応 #719649

反応方程式

4-[5-(2-amino-5-bromo-pyridin-3-yl)-[1,3,4]oxadiazol-2-yl]-piperidine-1-carboxylic acid tert-butyl ester

K2CO3

4-tolyl boronic acid

→

title compound

4-[5-(2-Amino-5-p-tolyl-pyridin-3-yl)-[1,3,4]oxadiazol-2-yl]-piperidine-1-carboxylic acid tert-butyl ester

溶媒

water

dioxane

water

反応条件

後処理

1. 1
   その他The reaction mixture was degassed with N2 for 20 min
2. 2
   抽出extracted with ethyl acetate (3×30 mL) and organic layer
3. 3
   洗浄was washed with brine
4. 4
   乾燥dried the organic layer over anhydrous sodium sulphate
5. 5
   濃縮concentrated under reduced pressure
6. 6
   その他to affords the crude product
7. 7
   その他Crude was purified by column chromatography
8. 8
   洗浄eluted with 35% ethyl acetate in petroleum ether

実験手順

To a solution of 4-[5-(2-amino-5-bromo-pyridin-3-yl)-[1,3,4]oxadiazol-2-yl]-piperidine-1-carboxylic acid tert-butyl ester (500 mg, 1.179 mmol) in dioxane (20 mL) and water (10 mL) were added K2CO3 (488 mg, 3.537 mmol) and 4-tolyl boronic acid (179 mg, 1.297 mmol) in a sealed tube. The reaction mixture was degassed with N2 for 20 min, then Pd(PPh3)4 (136 mg, 0.118 mmol) was added to the reaction mixture at RT, The reaction mixture temperature was raised to 100° C., stirred for 18 h at 100° C. The reaction mixture was diluted with water (30 mL) extracted with ethyl acetate (3×30 mL) and organic layer was washed with brine, dried the organic layer over anhydrous sodium sulphate and concentrated under reduced pressure to affords the crude product. Crude was purified by column chromatography using 100-200 mesh silica gel compound eluted with 35% ethyl acetate in petroleum ether to afford the title compound as a white solid.

出典