Реакция #8188

Уравнение реакции

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

Выход 93.3%

Растворители

tetrahydrofuran

brine

Условия реакции

Обработка

1. 1
   ТемператураThe mixture is refluxed for 22 hours
2. 2
   Температураcooled
3. 3
   Экстракцияextracted three times with ethyl acetate
4. 4
   СушкаThe combined organics are dried over anhydrous sodium sulfate
5. 5
   Фильтрацияfiltered
6. 6
   Другоеevaporated in vacuo
7. 7
   ДругоеThe residue is purified
8. 8
   Промывкаsilica gel chromatography (hexane/20% ethyl acetate, hexane gradient elution)

Методика

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).

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