Sodium Iodide → 8-Benzyloxy-5-((R)-1-(tert-butyldimethylsilanyloxy)-2-{2-[4-(3-chlorophenoxy)phenyl]ethylamino}ethyl)-1H-quinolin-2-one

Participants

Reaction Steps

A slurry of the product of step (b) (1.39 g), 8-(benzyloxy)-5-[(R)-2-bromo-1-(tert-butyldimethylsilanyloxy)ethyl]-1H-quinolin-2-one (2.49 g), sodium iodide (1.14 g) and potassium carbonate (2.11 g) in DMSO (7 mL) was heated at 90° C. for 5 h. The solution was allowed to cool, diluted with dichloromethane (60 mL) and washed with water (4×30 mL) then brine (40 mL). The organics were dried over sodium sulfate, concentrated in vacuo and the residue purified by reverse phase HPLC to afford the title intermediate (1.85 g) as a clear oil. m/z: [M+H+] calcd for C38H43ClN2O4Si 655.3. found 655.5.

Provenance & Evidence