2-Fluoro-6-(1h-imidazol-2-yl)pyridine → HCID 22260382, compound

Participants

Reaction Steps

To a solution of 2-chloromethyl-3,5-diethoxy-pyridine (174 mg, 0.69 mmol) in DMF (5 mL) is added 2-fluoro-6-(1H-imidazol-2-yl)-pyridine (112 mg, 0.69 mmol), and the reaction is stirred at room temperature overnight. The reaction mixture is diluted with water, extracted with EtOAc, washed with brine, dried over Na2SO4, and concentrated. The residue is purified by column chromatography eluting with 8% MeOH—CH2Cl2 containing few drops of NH4OH to afford 2-[2-(6-fluoro-pyridin-2-yl)-imidazol-1-yl methyl]-3,5-diethoxy-pyridine (118 mg, 49%); 1H NMR (300 MHz, CDCl3): 8.06 (dd, J=5.1, 2.4 Hz, 1H), 7.81 (t, J=7.9 Hz, 1H), 7.75 (d, J=2.4 Hz, 1H), 7.09 (s, 1H), 7.04 (s, 1H), 6.80 (dd, J=5.1, 2.7 Hz, 1H), 6.65 (d, J=2.4 Hz, 1H), 5.95 (s, 2H), 4.02 (q, J=6.9 Hz, 2H), 3.90 (q, J=6.9 Hz, 2H), 1.39 (t, J=6.9 Hz, 2H), 1.16 (t, J=6.9 Hz, 2H), m/z 343 [M+1].

Provenance & Evidence