反応 #2166358

反応方程式

4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamine

3,4-dimethoxybenzaldehyde

1g

2-{3-[(4-carbamimidoylphenylamino)-(2-fluoro-4,5-dimethoxyphenyl)methyl]5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl}benzoic Acid trifluoroacetate

trimethylsilyl cyanide

Yb(OTf)3

→

title compound

(3,4-dimethoxyphenyl)-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]acetonitrile

溶媒

ethyl acetate

dichloromethane

反応条件

後処理

1. 1
   ろ過was filtered through celite
2. 2
   洗浄the celite was washed with 200 ml of ethyl acetate
3. 3
   洗浄washed with water and saturated brine
4. 4
   乾燥dried over anhydrous magnesium sulfate
5. 5
   ろ過The desiccating agent was filtered off
6. 6
   濃縮the filtrate was concentrated under reduced pressure
7. 7
   その他The residue was purified by silica gel column chromatography (ethyl acetate-heptane)

実験手順

After adding 0.887 g of 4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamine, 0.831 g of 3,4-dimethoxybenzaldehyde, 1g of MS3A and 1 ml of trimethylsilyl cyanide to a solution of 0.31 g of Yb(OTf)3 in 20 ml of dichloromethane under a nitrogen atmosphere, the mixture was stirred at room temperature for 22 hours. After then adding 200 ml of ethyl acetate to the reaction mixture, it was filtered through celite and the celite was washed with 200 ml of ethyl acetate. The organic layers were combined and washed with water and saturated brine, and then dried over anhydrous magnesium sulfate. The desiccating agent was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-heptane) to give the title compound (1.75 g) as a light yellow solid.

出典