反応 #8188

反応方程式

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

収率 93.3%

溶媒

tetrahydrofuran

brine

反応条件

後処理

1. 1
   温度The mixture is refluxed for 22 hours
2. 2
   温度cooled
3. 3
   抽出extracted three times with ethyl acetate
4. 4
   乾燥The combined organics are dried over anhydrous sodium sulfate
5. 5
   ろ過filtered
6. 6
   その他evaporated in vacuo
7. 7
   その他The residue is purified
8. 8
   洗浄silica gel chromatography (hexane/20% ethyl acetate, hexane gradient elution)

実験手順

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).

出典