Toluene → HCID 15947595, compound

Participants

Reaction Steps

To a 25 mL round bottom flask attached with Vigreux column was added 2-[2-(2,6-Dichloro-phenyl)-1-(3′-methanesulfonyl-biphenyl-4-yl)-1H-imidazol-4-yl]-propan-2-ol (383 mg, 764 μmol), anhydrous toluene (8 mL) and acetic acid (3.5 mL). The reaction solution was allowed to stir at reflux for 1.5 hr. The cooled reaction solution was concentrated in vacuo, and the residue was taken into EtOAc (200 mL) and washed with aq NaHCO3 (100 mL×2) and aq. NaCl (100 mL). The organic phase was partitioned, dried over Na2SO4, filtered and concentrated in vacuo. The crude product was chromatographed through a 25 g SiO2 column using a mobile gradient of 100% Hx to 80% EtOAc to provide 288 mg (78% yield) of title compound. 1H NMR (400 MHz, DMSO-d6): δ 8.15 (br s, 1H), 8.08-7.97 (m, 2H), 7.92 (d, 1H), 7.89 (d, 2H), 7.75 (t, 1H), 7.64-7.57 (m, 3H), 7.43 (d, 2H), 5.77 (br s, 1H), 5.10 (br s, 1H), 3.29 (s, 3H), 2.11 (s, 3H); MS (ES): 483.1, 485.1 [M+H]+.

Provenance & Evidence