Sodium hydride → 5-chloro-6,7-bis((4-methoxybenzyl)oxy)-2-(2-(pyrrolidin-1-yl)ethyl)-3,4-dihydroisoquinolin-1(2H)-one

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Reaction Steps

To the solution of 5-chloro-6,7-bis((4-methoxybenzyl)oxy)-3,4-dihydroisoquinolin-1(2H)-one (1.017 g, 2.241 mmol) in N,N-dimethylformamide (DMF) (10 ml) was added sodium hydride (0.179 g, 4.48 mmol). Stirred at rt for 10 min. 1-(2-Chloroethyl)pyrrolidine (0.329 g, 2.465 mmol) (first freed as free base with MP-carbonate resin) was added and the mixture was heated at 40° C. for 12 h. Mixture extracted with EtOAc, washed with water, NaCl, dried over magnesium sulfate. Chromotagraphed eluting with 0-10% methanol:dichloromethane to give 5-chloro-6,7-bis((4-methoxybenzyl)oxy)-2-(2-(pyrrolidin-1-yl)ethyl)-3,4-dihydroisoquinolin-1(2H)-one (420 mg, 0.762 mmol, 34.0% yield). LCMS (M+H)+: 551.0

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