반응 #73475

반응 방정식

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

수율 28.6%

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

수율 28.6%

용매

toluene

반응 조건

후처리

1. 1
   기타The solution was degassed twice
2. 2
   기타The mixture was evaporated
3. 3
   workup.DISSOLUTIONredissolved in 50 mL of dichloromethane
4. 4
   세척washed twice with 50 mL of saturated aqueous sodium bicarbonate solution
5. 5
   건조The organic phase was dried over magnesium sulphate
6. 6
   여과filtered
7. 7
   농축concentrated
8. 8
   기타purified by silica gel chromatography (dichloromethane:methanol)

실험 절차

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+).

출처