반응 #8188

반응 방정식

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

수율 93.3%

용매

tetrahydrofuran

brine

반응 조건

후처리

1. 1
   온도The mixture is refluxed for 22 hours
2. 2
   온도cooled
3. 3
   추출extracted three times with ethyl acetate
4. 4
   건조The combined organics are dried over anhydrous sodium sulfate
5. 5
   여과filtered
6. 6
   기타evaporated in vacuo
7. 7
   기타The residue is purified
8. 8
   세척silica gel chromatography (hexane/20% ethyl acetate, hexane gradient elution)

실험 절차

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).

출처