Sodium Iodide → HCID 14836990, compound

Participants

Reaction Conditions

Reaction Steps

2-Hydroxy-5-bromopyridine (5.000 g, 28.74 mmol), potassium carbonate (14.30 g, 9.283 mL, 103.5 mmol), and sodium iodide (1.077 g, 7.185 mmol) were suspended in chloroacetonitrile (10.85 g, 9.095 mL, 143.7 mmol). The reaction mixture was heated to 60° C. and stirred for 2 hours. The reaction mixture was allowed to cool to room temperature, filtered, and the filtercake was washed with dichloromethane and ethyl acetate. The filtrate was concentrated and purified on 120 g of silica gel utilizing a gradient of 0-100% ethyl acetate in hexanes over 45 minutes to yield the pure product as a beige solid (4.1 g, 67%). 1H NMR (400.0 MHz, DMSO-d6) δ 8.11 (d, J=2.7 Hz, 1H), 7.63 (dd, J=2.8, 9.8 Hz, 1H), 6.49 (d, J=9.8 Hz, 1H), 4.94 (s, 2H).

Provenance & Evidence