Reacción #8188

Ecuación de reacción

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

sodium carbonate

4-trifluoromethylbenzeneboronic acid

→

{1,1-dimethyl-2-[7-(4-trifluoromethyl-phenyl)-1 H-indol-3-yl]-ethyl}-carbamic acid tert-butyl ester

Rendimiento 93.3%

Disolventes

tetrahydrofuran

brine

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe mixture is refluxed for 22 hours
2. 2
   Temperaturacooled
3. 3
   Extracciónextracted three times with ethyl acetate
4. 4
   SecadoThe combined organics are dried over anhydrous sodium sulfate
5. 5
   Filtraciónfiltered
6. 6
   Otroevaporated in vacuo
7. 7
   OtroThe residue is purified
8. 8
   Lavadosilica gel chromatography (hexane/20% ethyl acetate, hexane gradient elution)

Procedimiento

To a solution of trifluoro-methanesulfonic acid 3-(2-tert-butoxycarbonylamino-2-methyl-propyl)-1H-indol-7-yl ester (305 mg, 0.699 mmol) in tetrahydrofuran (4.5 mL) is added sodium carbonate (1 mL, 2M, 2 mmol), tetrakis(triphenylphosphine)-palladium (32 mg, 0.0280 mmol) and 4-trifluoromethylbenzeneboronic acid (0.1 99 g, 1.05 mmol). The mixture is refluxed for 22 hours, then cooled, diluted with brine and extracted three times with ethyl acetate. The combined organics are dried over anhydrous sodium sulfate, filtered and then evaporated in vacuo. The residue is purified using silica gel chromatography (hexane/20% ethyl acetate, hexane gradient elution) to give 282 mg of {1,1-dimethyl-2-[7-(4-trifluoromethyl-phenyl)-1 H-indol-3-yl]-ethyl}-carbamic acid tert-butyl ester (93%). FDMS m/e=433 (M++1).

Fuente