Potassium Carbonate → 3-Mppts

Participants

Reaction Conditions

Reaction Steps

The resultant N-(3-(2-methoxyphenoxy)phenyl)pyrid-3-ylmethylamine was dissolved in 2:1 1,2-dichloroethane/pyridine (6 mL) under nitrogen, cooled (5° C.), and treated with 2,2,2-trifluoroethylsulfonyl chloride (300 mg, 1.64 mmol). After one hour at 5° C., the mixture was allowed to warm to room temperature and stirred for 18 h. The product mixture was treated with anhydrous potassium carbonate (500 mg), stirred 30 min, filtered, and the filtrate concentrated in vacuo. The residue was chromatographed on silica gel (eluted with 2:1 dichloromethane/ethyl acetate) to afford the title compound (226 mg, 50%) as a viscous pale amber oil. The hydrochloride salt was obtained by treatment of this material in methanol with ethereal HCl. 1H NMR: 8.49 (d,1H,J=4 Hz), 8.29 (s,1H), 7.60-7.65 (m,1H), 7.20-7.25 (m,2H), 7.10-7.20 (m,1H), 6.97 (d,1H,J=8 Hz), 6.90 (m,2H), 6.80-6.85 (m,2H), 6.76 (m,1H), 4.82 (s,2H), 3.70-3.85 (m,2H), 3.75 (s,3H). MS calcd. 452.4; MS (M+1) 453.3

Provenance & Evidence