Pyridine → HCID 178527392, compound

To a solution of 4-(2-(2-(1-trityl-1H-imidazol-4-yl)phenoxy)ethyl)aniline (80 mg, 0.153 mmol) in dichloromethane (4 mL) was added pyridine (24 μL, 0.307 mmol) followed by benzylsulfonyl chloride (32 mg, 0.169 mmol). The mixture was stirred at room temperature for 16 h and concentrated. The solvent was removed under reduced pressure and the crude was dissolved in methanol (4 mL) and acetic acid (1 mL). The reaction mixture was heated at 80° C. for 2 h. The reaction mixture was basified with aqueous 10% NaOH and the aqueous layer extracted with ethyl acetate (2×30 mL). The combined organic extracts were washed with brine (15 mL), dried over Na2SO4 and concentrated. The residue was purified by flash column chromatography using 5% MeOH/dichloromethane as an eluent at afford the desired product as a yellowish solid (52 mg, 0.120 mmol, 79%). 1H NMR: 3.16 (t, 2H, J=63.4 Hz), 4.28 (t, 2H, J=6.4 Hz), 4.36 (s, 2H), 6.92 (t, 1H, J=6.8 Hz), 7.02 (s, 1H), 7.11 (d, 3H, J=7.2 Hz), 7.19 (s, 2H), 7.28-7.31 (m, 5H), 7.41 (s, 1H), 7.62 (s, 1H), 8.04 (s, 1H), 9.71 (s, 1H).