Methyl iodide → 1-methyl-3-(3-trifluoromethyl-7,8-dihydro-5H-[1,6]naphthyridine-6-carbonyl)-3H-imidazol-1-ium iodide

Participants

Reaction Steps

To a suspension of imidazol-1-yl-(3-trifluoromethyl-7,8-dihydro-5H-[1,6]naphthyridin-6-yl)-methanone (preparation #1) (1.28 g, 4.32 mmol) in MeCN (10 mL) was added methyl iodide (1.1 mL, 17 mmol) and the reaction mixture was stirred at ambient temperature for about 2 h. Additional methyl iodide (0.5 mL, 8 mol) was added and stirring resumed for about 16 h. The reaction mixture was concentrated in vacuo to afford 1-methyl-3-(3-trifluoromethyl-7,8-dihydro-5H-[1,6]naphthyridine-6-carbonyl)-3H-imidazol-1-ium iodide (1.89 g, 100%) as an orange solid which was used in subsequent reactions without further purification. RP-HPLC (Table 1, Method d) Rt 1.77 min; m/z: (M+H)+ 311.

Provenance & Evidence