Ethyl bromoacetate → (2-Methyl-4-pyrrolidin-1-yl-quinolin-7-yloxy)-acetic acid ethyl ester

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Reaction Steps

To a cooled (0° C.) solution of 2-methyl-4-pyrrolidin-1-yl-quinolin-7-ol (797 mg, 3.49 mmol) in dimethylformamide (13 mL) was added sodium hydride (ca. 60% in oil, 168 mg, 4.19 mmol). After 30 min at 0° C., ethyl bromoacetate (0.5 mL, 4.50 mmol) was injected. After 2 h30, an aqueous solution of NaHCO3 was added and the aqueous layer was extracted with dichloromethane. The combined organic phases were washed with brine and water and then dried over sodium sulfate. After filtration, solvents were removed in a high vacuum. The brown oil was triturated with diethylether. After filtration, the solid was dried in a high vacuum to give 660 g (60.2%) of (2-methyl-4-pyrrolidin-1-yl-quinolin-7-yloxy)-acetic acid ethyl ester as a light brown solid. ISP mass spectrum, m/e: 315.4 (M+1 calculated for C18H22N2O3: 315.4).

Provenance & Evidence