Réaction #8188

Équation de réaction

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

Rendement 93.3%

Solvants

tetrahydrofuran

brine

Conditions de réaction

Traitement

1. 1
   TempératureThe mixture is refluxed for 22 hours
2. 2
   Températurecooled
3. 3
   Extractionextracted three times with ethyl acetate
4. 4
   SéchageThe combined organics are dried over anhydrous sodium sulfate
5. 5
   Filtrationfiltered
6. 6
   Autreevaporated in vacuo
7. 7
   AutreThe residue is purified
8. 8
   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 (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).

Source