Pyridine → HCID 19001394, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 0.15 g (0.0005 mol) of bis(trichloromethyl)carbonate, 20 mL of methylene chloride and 0.39 mL (0.0048 mol) of pyridine was added 0.5 g (0.0015 mol) of the product from Step H at 0° C. The resulting mixture was stirred at 0° C. for 2 hours and then 0.21 g (0.0016 mol) of 5-amino-2-chloro pyridine was added. The resulting mixture was stirred at room temperature for 12 hours and then 10 mL of ethanol followed by 3 g of silica gel were added and the solvent was removed. Flash chromatography of the residue on silica gel using 2:1 hexanes-EtOAc gave 0.28 g of an off-white solid that melted at 236°-238° C. 1H NMR (CDCl3, 200 MHz) δ3.77 (s, 3H), 3.85 (d, 1H), 4.24 (d, 1H), 4.53 (d, 1H), 5.07 (d, 1H), 7.20-7.35 (m, 3H), 7.98 (d, 1H), 8.02 (s, 1H), 8.12 (dd, 1H), 8.42 (d, 1H).

Provenance & Evidence