Sodium hydride → HCID 71117584, compound

Participants

Reaction Steps

Sodium hydride (60% in mineral oil, 60 mg, 1.44 mmol) was added to a solution of 1-(1-(4-fluorophenyl)-4-methyl-2-((2,3,6-trifluorobenzyl)thio)-1H-imidazol-5-yl)ethanol (62) (190 mg, 0.48 mmol) in THF (5 mL) and the reaction was allowed to stir at room temperature for 20 min. 4-(bromomethyl)pyridine hydrobromide (146 mg, 0.576 mmol) was added to the reaction mixture and heated to 70° C. overnight. The reaction was cooled to room temperature, quenched with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (0-100% EtOAc in hexanes) to afford 4-((1-(1-(4-fluorophenyl)-4-methyl-2-((2,3,6-trifluorobenzyl)thio)-1H-imidazol-5-yl)ethoxy)methyl)pyridine (628). 1H NMR (400 MHz, CDCl3) δ: 8.56 (d, J=6.0, 2H), 7.20-7.17 (m, 4H), 7.04-6.96 (m, 3H), 6.74-6.68 (m, 1H), 5.31-5.15 (m, 2H), 4.63 (q, J=6.4, 1H), 4.48 (d, J=13.5, 1H), 4.32 (d, J=13.5, 1H), 2.19 (s, 3H), 1.45 (d, J=6.4, 3H). LC-MS ESI m/z; found 488.2 [M+H]+.

Provenance & Evidence