Methanol → 1-(4-Bromopyridin-2-yl)-4-methoxybutylamine

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Reaction Steps

A solution of 4.3 g of 4-bromopyridine-2-carbonitrile [62150-45-2] in 10 ml of tetrahydrofuran is added to a solution of 8.79 g of 3-methoxypropylmagnesium chloride [14202-12-1] in 10 ml of tetrahydrofuran. The reaction solution is stirred at room temperature for 10 minutes and then 50 ml of methanol are added. 2.7 g of sodium borohydride are added to the solution over the course of 30 minutes, and the mixture is stirred at room temperature for 2.5 hours. It is diluted with ethyl acetate and basified with 1M sodium hydroxide solution. The phases are separated. The aqueous phase is extracted with ethyl acetate (2×). The combined organic phases are evaporated. The crude title compound is obtained as an orange oil from the residue. Rt=2.47 (Gradient I).

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