Dimethylamine → (S)-2-(5-bromo-2-((dimethylamino)methyl)-7-methylquinolin-6-yl)-2-tert-butoxyethyl pivalate

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of (S)-5-bromo-6-(1-tert-butoxy-2-(pivaloyloxy)ethyl)-2,7-dimethylquinoline 1-oxide (25 mg, 0.055 mmol) in toluene (3 mL) was added benzenesulfonyl chloride (0.06 mL, 0.24 mmol). The mixture was stirred at 110° C. for 16 hours, then cooled to room temperature. Dimethylamine (2 mL 2 M solution in methanol, excess) was added. The mixture was stirred at room temperature for 16 h, then diluted in ethyl acetate (30 mL), washed with NaHCO3 solution, water and brine, dried over Na2SO4, filtered and concentrated in vacuo. The obtained residue was purified by HPLC to provide the desired product as a white solid (11 mg, 42%). LCMS-ESI+ (m/z): 479.3, 481.3 (M+H)+.

Provenance & Evidence