Methyl iodide → HCID 15228773, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 3-[N-(p-chlorobenzyl)-3-(t-butylthio)-5-(quinolin-2-yl methoxy) indol-2-yl]-2,2-dimethylpropanoate (420 mg) (EP 419,049, Ex. 1, Step D) in THF (10 mL) at -78° C. was added 0.6M potassium hexamethyldisilazane in toluene (1.75 mL) and stirred at -78° C. for 5 min. Then iodomethane (87 ml) was added followed 15 min later by more 0.6M KHMDS in toluene (1.75 mL). The mixture was finally stirred at -78° C. for 30 min. The reaction mixture was poured into 25% NH4OAc (100 mL), extracted with ethyl acetate (2×100 mL), washed with brine (100 mL), and dried (MgSO4). The filtrate was evaporated to dryness and the residue was chromatographed on flash silica gel using ethyl acetate:hexane (15:85) as eluant to give the title product as a foam.

Provenance & Evidence