Dimethylacetamide → 3-Chloro-5-(naphthalen-2-yl)isonicotinonitrile

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A mixture of 3,5-dichloroisonicotinonitrile (0.300 g, 1.734 mmol), naphthalen-2-ylboronic acid (0.328 g, 1.908 mmol), potassium phosphate (0.736 g, 3.47 mmol) and palladium tetrakis(triphenylphosphine) (0.100 g, 0.087 mmol) was pumped and backfilled with nitrogen 3 times. N,N-Dimethylacetamide (6 mL) was added. The mixture was again pumped and backfilled with nitrogen 3 times. The reaction tube was sealed and heated to 150° C. under microwave for 30 min. The mixture was diluted with ethyl acetate (80 mL), washed with 1:1 mixture of brine and water (30 mL), brine (30 mL), dried (MgSO4) and concentrated. Silica gel chromatography, loading with toluene and eluting with 10-35% ethyl acetate in hexanes, gave 3-chloro-5-(naphthalen-2-yl)isonicotinonitrile as a white solid (240.5 mg, 46% yield). 1H NMR (400 MHz, CDCl3) δ ppm 8.83 (1H, s), 8.81 (1H, s), 8.00-8.15 (2H, m), 7.87-8.00 (2H, m), 7.67 (1H, dd, J=8.53, 2.01 Hz), 7.53-7.64 (2H, m); MS (ES+) m/z: 265 (M+H); LC retention time: 4.066 min (analytical HPLC Method A).

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