6-Chloropyridine-2-carbonitrile → 1-(6-Chloropyridin-2-yl)cyclopropan-1-amine

Participants

Reaction Steps

To a solution of 6-Chloro-pyridine-2-carbonitrile (500 mg, 3.61 mmol) in THF (45 mL) was added titanium isopropoxide (1.59 mL, 5.41 mmol) in one portion followed by ethylmagnesium bromide (3 M in Et2O, 3.6 mL, 11 mmol) slowly over 5 min. The reaction was stirred for 4 then quenched by the addition of water (5 mL). The mixture was filtered through a pad of diatomaceous earth and the filtrate was concentrated. The resulting material was purified first by flash chromatography (silica, 5→10% MeOH/CH2Cl2) and then by reversed phase HPLC (1→95% MeCN/H2O+0.1% TFA) to give 86 mg of the title compound presumably as the bis-TFA salt, m/z 169.59 [M+1]+.

Provenance & Evidence