反応 #8201

反応方程式

Trifluoro-methanesulfonic acid 3-(2-tert-butoxycarbonylamino-2-methyl-propyl)-1H-indol-7-yl ester

methyl acrylate

triethylamine

ethyl acetate

→

3-[3-(2-tert-butoxycarbonylamino-2-methyl-propyl)-1H-indol-7-yl]-acrylic acid methyl ester

収率 82.0%

溶媒

dimethylformamide

brine

反応条件

後処理

1. 1
   温度The reaction is cooled to room temperature
2. 2
   workup.ADDITIONpoured into a separatory funnel
3. 3
   抽出the aqeous layer is extracted with ethyl acetate (50 mL)
4. 4
   洗浄The combined organic layers are washed with brine
5. 5
   乾燥dried (Na2SO4)
6. 6
   その他evaporated
7. 7
   その他The residue is purified

実験手順

Trifluoro-methanesulfonic acid 3-(2-tert-butoxycarbonylamino-2-methyl-propyl)-1H-indol-7-yl ester (200 mg, 0.46 mmol), methyl acrylate (80 mg, 0.92 mmol) and triethylamine (0.40 mL, 3.0 mmol) is stirred in dimethylformamide (2.0 mL) at room temperature for 30 minutes. Dichlorobis(triphenylphosphine)palladium (31 mg, 0.045 mmol) is added, the reaction mixture is heated to 90° C. and allowed to stir overnight. The reaction is cooled to room temperature, poured into a separatory funnel containing ethyl acetate and brine (50 mL each) and the aqeous layer is extracted with ethyl acetate (50 mL). The combined organic layers are washed with brine, dried (Na2SO4) and evaporated. The residue is purified using silica gel chromatography (20% ethyl acetate/hexane) to give 140 mg of 3-[3-(2-tert-butoxycarbonylamino-2-methyl-propyl)-1H-indol-7-yl]-acrylic acid methyl ester (82%). FDMS mie =372.2 (M++1).

出典