Hydrochloric Acid → 2-Bromo-6-(1-pyrrolidin-1-ylethyl)pyridine

Participants

Reaction Conditions

Reaction Steps

A solution of 1-(6-bromopyridin-2-yl)ethanol (Example 3, Step 1) (0.5 g, 2.48 mmol) in tetrahydrofuran (4 mL) at 0° C. was charged with triethyl amine (1.04 mL, 7.42 mmol), and then a solution of methanesulfonic anhydride (0.56 g, 3.22 mmol) in tetrahydrofuran (6 mL) added over 30 minutes. The reaction mixture was stirred at 0° C. for 2 hrs and then pyrrolidine (0.21 mL, 2.48 mmol) was added and the mixture was warmed to room temperature. After sixteen days the reaction mixture was poured into aqueous hydrogen chloride (1 M, 10 mL) and dichloromethane (10 mL) The layers were separated and the organic layer was extracted with aqueous hydrogen chloride (1 M, 10 mL). The combined aqueous layers were neutralized with aqueous sodium hydroxide (2 M) until pH=10 and then extracted with dichloromethane (3×20 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated to afford the title compound.

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