تفاعل #8189

معادلة التفاعل

trifluoro-methanesulfonic acid 3-(2-tert-butoxycarbonylamino-2-methyl-propyl)-1H-indol-7-yl ester

triethylamine

3-thiopheneboronic acid

→

[1,1-dimethyl-2-(7-thiophen-3-yl-1H-indol-3-yl)-ethyl]-carbamic acid tert-butyl ester

المردود 69.0%

المذيبات

dimethylformamide

brine

ethyl acetate

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe mixture is refluxed for
2. 2
   درجة الحرارة22 hours, then cooled
3. 3
   غسيلThe organic phase is washed 7 times with brine
4. 4
   تجفيفThe 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 (340 mg, 0.779 mmol) in dimethylformamide (5 mL) is added triethylamine (0.14 mL, 1.01 mmol), tetrakis(triphenylphosphine)-palladium (36 mg, 0.0312 mmol) and 3-thiopheneboronic acid (130 mg, 1.01 mmol). The mixture is refluxed for. 22 hours, then cooled and diluted with brine and ethyl acetate. The organic phase is washed 7 times with brine. The 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 198 mg of [1,1-dimethyl-2-(7-thiophen-3-yl-1H-indol-3-yl)-ethyl]-carbamic acid tert-butyl ester (69%). FDMS m/e=371 (M++1).

المصدر