تفاعل #8201

معادلة التفاعل

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

المردود 82.0%

المذيبات

dimethylformamide

brine

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe reaction is cooled to room temperature
2. 2
   workup.ADDITIONpoured into a separatory funnel
3. 3
   استخلاصthe aqeous layer is extracted with ethyl acetate (50 mL)
4. 4
   غسيلThe combined organic layers are washed with brine
5. 5
   تجفيفdried (Na2SO4)
6. 6
   أخرىevaporated
7. 7
   أخرىThe residue is purified

الإجراء التجريبي

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).

المصدر