Reaktion #8201

Reaktionsgleichung

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

Ausbeute 82.0%

Lösungsmittel

dimethylformamide

brine

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction is cooled to room temperature
2. 2
   workup.ADDITIONpoured into a separatory funnel
3. 3
   Extraktionthe aqeous layer is extracted with ethyl acetate (50 mL)
4. 4
   WaschenThe combined organic layers are washed with brine
5. 5
   Trocknendried (Na2SO4)
6. 6
   Sonstigeevaporated
7. 7
   SonstigeThe residue is purified

Vorschrift

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).

Quelle