Reacción #49498

Ecuación de reacción

4-hydroxy-7-(1-(tert-butoxycarbonyl)-5-[4-(2-tert-butyldimethylsilyloxyethyl)pyperazin-1-ylmethyl]indol-2-yl)isoindolinone

triethylamine

trifluoromethanesulfonyl chloride

→

4-trifluoromethanesulfonyloxy-7-{1-(tert-butoxycarbonyl)-5-[4-(2-tert-butyldimethylsilyloxyethyl)pyperazin-1-ylmethyl]indol-2-yl}isoindolinone

Rendimiento 77.0%

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooling
2. 2
   Otrofollowed by purification by preparative thin-layer chromatography (chloroform/methanol=13/1)

Procedimiento

In a similar manner to Step 1 of Example 299, 4-hydroxy-7-(1-(tert-butoxycarbonyl)-5-[4-(2-tert-butyldimethylsilyloxyethyl)pyperazin-1-ylmethyl]indol-2-yl)isoindolinone (150 mg, 0.240-mmol) was suspended in dichloromethane (6.0 mL), and the suspension was treated with triethylamine (0.167 mL, 1.20 mmol) and trifluoromethanesulfonyl chloride (0.046 mL, 0.43 mmol) under ice-cooling, followed by purification by preparative thin-layer chromatography (chloroform/methanol=13/1) to obtain 4-trifluoromethanesulfonyloxy-7-{1-(tert-butoxycarbonyl)-5-[4-(2-tert-butyldimethylsilyloxyethyl)pyperazin-1-ylmethyl]indol-2-yl}isoindolinone (139 mg, yield 77%).

Fuente