Imidazole → HCID 71547905, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-(5-(4-((methoxymethoxy)methyl)phenyl)pyridin-2-yl)propyl methanesulfonate (0.1 g, 0.27 mmol), 1H-imidazole (0.037 g, 0.54 mmol) and triethylamine (0.07 mL, 0.54 mmol) in THF (15 mL) was stirred and refluxed at 65° C. for 12 h, cooled to room temperature, poured into ice water (50 mL) and extracted with EtOAc (2×50 mL). The organic layer was separated, dried (Na2SO4), and the solvent was evaporated under vacuo. The resulting residue was purified by preparative TLC using 5% methanol in dichloromethane and isolated as light green viscous liquid (0.04 g, 44% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.86 (s, 1H), 8.06 (dd, 1H), 7.81 (s, 1H), 7.69 (d, 2H), 7.44 (d, 2H), 7.37 (d, 1H), 7.30 (s, 1H), 5.36 (q, 1H), 4.65 (s, 2H), 4.56 (s, 2H), 3.30 (s, 3H), 2.25 (m, 2H), 0.81 (t, 3H). LC-MS: m/z 338.2 [M+H]+.

Provenance & Evidence