تفاعل #1159773

معادلة التفاعل

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

triethylamine

2,4-bistrifluoromethylbenzeneboronic acid

→

{2-[7-(2,4-Bis-trifluoromethyl-phenyl)-1H-indol-3-yl]-1,1-dimethyl-ethyl}-carbamic acid tert-butyl ester

المردود 89.2%

المذيبات

dimethylformamide

brine

ethyl acetate

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةcooled
2. 2
   غسيلThe organics are washed seven times with brine
3. 3
   تجفيفthen dried over anhydrous sodium sulfate
4. 4
   ترشيحfiltered
5. 5
   أخرىevaporated in vacuo
6. 6
   أخرىThe residue is purified
7. 7
   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 (262 mg, 0.600 mmol) in dimethylformamide (3.5 mL) is added triethylamine (0.11 mL, 0.780 mmol), tetrakis(triphenylphosphine)-palladium (28 mg, 0.0240 mmol) and 2,4-bistrifluoromethylbenzeneboronic acid (201 mg, 0.780 mmol). The mixture is heated to 100° C. for 20 hours, then cooled, diluted with brine and ethyl acetate. The organics are washed seven times with brine then dried over anhydrous sodium sulfate, filtered and evaporated in vacuo. The residue is purified using silica gel chromatography (hexane/20% ethyl acetate, hexane gradient elution) to give 268 mg of {2-[7-(2,4-Bis-trifluoromethyl-phenyl)-1H-indol-3-yl]-1,1-dimethyl-ethyl}-carbamic acid tert-butyl ester (89%). FDMS m/e=501 (M++1). The title amine is prepared from {2-[7-(2,4-Bis-trifluoromethyl-phenyl)-1H-indol-3-yl]-1,1-dimethyl-ethyl}-carbamic acid tert-butyl ester as described above for Amine 1 (208 mg, 100%). FDMS m/e=401 (M++1).

المصدر