Methyl iodide → HCID 67422848, compound

Participants

Reaction Steps

To a solution of 1′-[2-(3H-imidazol-4-yl)-ethyl]-3,3″-dimethyl-1′,2′,3′,4′,5′,6′-hexahydro-[2,2′;6′,2″]terpyridine (167 mg, 0.46 mmol) in THF (5 mL) at 0° C. was added NaH (60%, 7 mg, 0.17 mmol). After 30 min at 0° C., MeI (10 mL, 0.15 mmol) was added and the reaction mixture was warmed to room temperature and stirred overnight. The next day the mixture was concentrated to afford a yellow foam. Purification by radial chromatography on silica gel (1 mm plate; using CH2Cl2/MeOH/NH4OH; 50:1:1→10:1:1) afforded the product as a yellow oil (23 mg, 41%). 1H NMR (CDCl3) δ 1.57-1.72 (m, 3H), 1.94-2.16 (m, 3H), 2.48-2.53 (m, 8H), 3.41 (s, 3H), 3.71 (s, 2H), 4.13 (d, 2H, J=9.0 Hz), 5.94 (br 2, 1H), 7.02-7.06 (m, 3H), 7.40 (d, 2H, J=9.0 Hz), 8.45 (br s, 2H). 13C NMR (CDCl3) δ 19.25, 23.34, 25.40, 32.42, 33.46, 50.08, 62.13, 115.93, 122.07, 132.50, 136.91, 138.83, 141.50, 147.32, 160.82. ES-MS m/z 376 [M+H]+. Anal. Calcd. for C1753H29N5.1.4H2O.0.4CH2Cl2: C, 64.65; H, 7.56; N, 16.11. Found: C, 65.01; H, 7.67; N, 15.99.

Provenance & Evidence