Imidazole → HCID 86730058, compound

Participants

Reaction Steps

To a stirred solution of (6-chloropyridin-3-yl)methanol (643 mg, 4.48 mmol) in DMF (15 mL) was added tert-butylchlorodimethylsilane (675 mg, 4.48 mmol) and imidazole (610 mg, 8.96 mmol). The reaction mixture was stirred at room temperature for 5 h, then diluted with 200 mL of ether, washed with saturated NaHCO3 solution, 10% LiCl solution, and brine. The solution was dried with anhydrous MgSO4, filtered and concentrated. The residue was purified by silica gel chromatography (hexane/EtOAc) to provide Preparation 47A (869 mg, 75%). HPLC: RT=3.623 min (H2O/MeOH with TFA, CHROMOLITH® ODS, 4.6×50 mm, gradient=4 min, wavelength=220 nm); MS(ES): m/z=258 [M+H+]; 1H NMR (400 MHz, DMSO-d6) δ 8.35 (d, J=1.8 Hz, 1H), 7.77 (dd, J=8.1, 2.4 Hz, 1H), 7.50 (d, J=8.4 Hz, 1H), 4.75 (s, 2H), 0.93-0.86 (m, 9H), 0.12-0.06 (m, 6H).

Provenance & Evidence