Methyl Ethyl Ketone → HCID 131735909, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-bromopyridin-2-amine (500 mg, 2.89 mmol), butan-2-one (611 μl, 6.82 mmol), and zinc chloride (0.5 M, 1.15 mL, 0.578 mmol) in acetonitrile (1.44 mL) was purged with Ar(g) for ˜5 minutes. The reaction was cooled to 0° C. and TMS-CN (775 μl, 5.78 mmol) was added dropwise. The reaction mixture was heated to 85° C. overnight. Upon cooling, the reaction mixture was diluted with water and extracted with dichloromethane (3×). The organic layer was concentrated under reduced pressure and the residue was purified by silica gel chromatography (ethyl acetate/hexanes) to yield 2-[(5-bromopyridin-2-yl)amino]-2-methylbutanenitrile. 1H NMR (500 MHz, CDCl3) δ 8.19 (d, J=3.2, 1H), 7.49 (dd, J=2.6, 8.9, 1H), 6.46 (d, J=9.6, 1H), 4.74 (s, 1H), 2.11-1.95 (m, 2H), 1.69 (s, 3H), 1.10-1.06 (m, 3H).

Provenance & Evidence