Réaction #8191

Équation de réaction

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

triethylamine

2,4-bistrifluoromethylbenzeneboronic acid

→

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

Rendement 89.2%

Solvants

dimethylformamide

brine

ethyl acetate

Conditions de réaction

Traitement

1. 1
   Températurecooled
2. 2
   LavageThe organics are washed seven times with brine
3. 3
   Séchagethen dried over anhydrous sodium sulfate
4. 4
   Filtrationfiltered
5. 5
   Autreevaporated in vacuo
6. 6
   AutreThe residue is purified
7. 7
   Lavagesilica gel chromatography (hexane/20% ethyl acetate, hexane gradient elution)

Mode opératoire

To a solution of trifluoro-methanesulfonic acid 3-(2-tert-butoxycarbonylamino-2-methyl-propyl)-1H-indol-7-yl ester (262 mg, 0.600 mmol) in dimethylformamide (3.5 mL) is added triethylamine (0.11 mL, 0.780 mmol), tetrakis(triphenylphosphine)-palladium (28 mg, 0.0240 mmol) and 2,4-bistrifluoromethylbenzeneboronic acid (201 mg, 0.780 mmol). The mixture is heated to 100° C. for 20 hours, then cooled, diluted with brine and ethyl acetate. The organics are washed seven times with brine then dried over anhydrous sodium sulfate, filtered and evaporated in vacuo. The residue is purified using silica gel chromatography (hexane/20% ethyl acetate, hexane gradient elution) to give 268 mg of {2-[7-(2,4-Bis-trifluoromethyl-phenyl)-1H-indol-3-yl]-1,1-dimethyl-ethyl}-carbamic acid tert-butyl ester (89%). FDMS m/e=501 (M++1).

Source