Acetic Acid → 6-chloro-N-(cyclopropylmethyl)-2-methylpyridin-3-amine

Participants

Reaction Steps

In a dry flask, 6-chloro-2-methylpyridin-3-amine (200 mg, 1.40 mmol) and cyclopropanecarbaldehyde (116 μl, 1.54 mmol) were taken up in 1,2-dichloroethane (5.6 ml) under argon. The resulting clear solution was stirred at room temperature for 1 hour. Sodium triacetoxyborohydride (0.47 g, 2.10 mmol) and acetic acid (160 μl, 2.81 mmol) were sequentially added to the reaction mixture, which was stirred as such for 24 hours. The reaction mixture was quenched with aqueous sodium bicarbonate and extracted three times with dichloromethane. All organic fractions were combined, dried over anhydrous magnesium sulfate, filtered, and concentrated. The resulting crude product was purified by silica gel chromatography (0-50% ethyl acetate/hexanes) to afford the title compound.

Provenance & Evidence