1,2-Dimethoxyethane → HCID 59251220, compound

Participants

Reaction Conditions

Reaction Steps

To a 50 mL round bottom flask attached with Vigreux column and magnetic stir bar was added 2-[1-(4-Bromo-phenyl)-2-(2-chloro-phenyl)-1H-imidazol-4-yl]-propan-2-ol (275 mg, 702 μmol), 3-methoxycarbonylphenyl boronic acid (164 mg, 913 μmol), PdCl2dppf (51 mg, 10 mol %), K2CO3 (290 mg, 2.11 mmol), 1,2-dimethoxyethane (13 mL) and H2O (1.5 mL). The reaction solution was allowed to stir at 70° C. for approximately 2 hrs. The reaction solution was diluted with EtOAc (150 mL) and filtered through a Celite padded Buchner funnel to remove spent Pd. The filtrate was transferred to a reparatory funnel and washed with aq NH4Cl (100 mL) and aq NaCl (100 mL). The organic phase was dried over Na2SO4, filtered, concentrated on the Rotavapor and chromatographed through a 25 g SiO2 column using a mobile phase gradient of 100% Hx to 90% EtOAc to afford 122 mg (39% yield) of product MS (ES): 446.3, 448.3 [M+H]+.

Provenance & Evidence