Imidazole → HCID 71547909, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 1H-imidazole (0.069 g, 1.0 mmol) in DMF (7 mL) was added 2-(1-bromoethyl)-5-(4-methoxyphenyl)pyridine (0.150 g, 0.50 mmol) and K2CO3 (354 mg, 2.5 mmol). The reaction was heated at 50° C. for about 3 h. The reaction mixture was diluted with water (100 mL) and extracted with ethyl acetate (2×100 mL). The combined organic extracts were washed with brine solution (10 mL), the organic layer was dried over Na2SO4 and concentrated under vacuum to obtain crude product. The crude product was purified by flash chromatography (silica gel, 100-200μ) using 2% methanol in DCM eluent to afford 2-(1-(1H-imidazol-1-yl)ethyl)-5-(4-methoxyphenyl)pyridine as an off-white solid (0.1 g, 69% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.80 (d, 1H), 7.99 (dd, 1H), 7.80 (s, 1H), 7.63 (d, 2H), 7.26 (s, 1H), 7.03 (d, 1H), 7.21 (d, 2H), 6.89 (s, 1H), 5.64-5.59 (m, 1H), 3.78 (s, 3H), 1.81 (d, 3H), LC-MS m/z calcd for [M+H]+ 280.14. found 280.2.

Provenance & Evidence