تفاعل #1359394

معادلة التفاعل

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)-1H-indol-3-yl]-ethyl}-carbamic acid tert-butyl ester

المردود 93.3%

المذيبات

tetrahydrofuran

brine

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe mixture is refluxed for 22 hours
2. 2
   درجة الحرارةcooled
3. 3
   استخلاصextracted three times with ethyl acetate
4. 4
   تجفيفThe combined organics are dried over anhydrous sodium sulfate
5. 5
   ترشيحfiltered
6. 6
   أخرىevaporated in vacuo
7. 7
   أخرىThe residue is purified
8. 8
   غسيلsilica gel chromatography (hexane/20% ethyl acetate, hexane gradient elution)

الإجراء التجريبي

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 (0.199 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)-1H-indol-3-yl]-ethyl}-carbamic acid tert-butyl ester (93%). FDMS m/e=433 (M++1).

المصدر