反応 #73475

反応方程式

6-bromo-isoquinoline

{1-[4-amino-1-(4-methoxy-phenyl)-cyclohexyl]-propyl}-carbamic acid benzyl ester

{1-[4-Amino-1-(4-methoxy-phenyl)-cyclohexyl]-propyl}carbamic acid benzyl ester

cesium carbonate

2,2′-bis(diphenylphosphino)-1,1′-binaphthyl

→

pure desired product

収率 28.6%

{1-[4-(Isoquinolin-6-ylamino)-1-(4-methoxy-phenyl)-cyclohexyl]-propyl}-carbamic acid benzyl ester

収率 28.6%

溶媒

toluene

反応条件

後処理

1. 1
   その他The solution was degassed twice
2. 2
   その他The mixture was evaporated
3. 3
   workup.DISSOLUTIONredissolved in 50 mL of dichloromethane
4. 4
   洗浄washed twice with 50 mL of saturated aqueous sodium bicarbonate solution
5. 5
   乾燥The organic phase was dried over magnesium sulphate
6. 6
   ろ過filtered
7. 7
   濃縮concentrated
8. 8
   その他purified by silica gel chromatography (dichloromethane:methanol)

実験手順

In 1 mL of absolute toluene were dissolved 66.0 mg (0.32 mmol) of 6-bromo-isoquinoline, 151 mg (380 μmol) of {1-[4-amino-1-(4-methoxy-phenyl)-cyclohexyl]-propyl}-carbamic acid benzyl ester (98), and 155 mg (476 μmol) of cesium carbonate. The solution was degassed twice, then 2.14 mg (9.5 μmol) of palladium acetate and 8.89 mg (14.3 μmol) of 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl were added and the reaction mixture was heated to 100° C. until complete conversion could be observed. The mixture was evaporated, then redissolved in 50 mL of dichloromethane and washed twice with 50 mL of saturated aqueous sodium bicarbonate solution. The organic phase was dried over magnesium sulphate, filtered, concentrated and purified by silica gel chromatography (dichloromethane:methanol) to give 48 mg of the pure desired product. Rt=1.38 min (Method 19). Detected mass: 524.4 (M+H+).

出典