تفاعل #45362

معادلة التفاعل

methyl [3,5-bis(trifluoromethyl)benzyl](2-iodo-5-trifluoromethyl-benzyl)carbamate

methyl [3,5-bis(trifluoromethyl)benzyl][2-iodo-5-(trifluoromethyl)benzyl]carbamate

EtOH

4-isoquinolineboronic acid

sodium carbonate

→

desired product

Methyl [3,5-bis(trifluoromethyl)benzyl][2-isoquinolin-4-yl-5-(trifluoromethyl)benzyl]carbamate

المذيبات

toluene

ظروف التفاعل

المعالجة

1. 1
   أخرىThe solution was degassed
2. 2
   workup.ADDITIONfollowed by the addition of a catalytic amount of tetrakis(triphenylphosphine)palladium
3. 3
   درجة الحرارةUpon cooling
4. 4
   أخرىthe solvent was removed in vacuo

الإجراء التجريبي

To a solution of methyl [3,5-bis(trifluoromethyl)benzyl](2-iodo-5-trifluoromethyl-benzyl)carbamate (41 mg, 0.070 mmol) (Example 5) in 3:2 EtOH:toluene, 4-isoquinolineboronic acid (18.2 mg, 0.105 mmol) and 2.5 M sodium carbonate (0.175 mmol) were added. The solution was degassed, followed by the addition of a catalytic amount of tetrakis(triphenylphosphine)palladium. The solution was stirred at 95-100° C. until completion of the reaction. Upon cooling, the solvent was removed in vacuo. The desired product was obtained by preparative thin layer chromatography using 25% acetone/hexane. 1H NMR (CDCl3, 500 MHz) δ 9.36 (s, 1H), 8.38 (s, 1H), 8.10-8.13 (m, 1H), 7.68-7.80 (m, 4H), 7.26-7.64 (m, 5H), 4.22-4.48 (m, 4H), 3.64-3.78 (m, 3H). LC-MS (M+1) 587.2 (3.48 min).

المصدر