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0 °C

To a 250 mL round bottom flask, purged with dry N2 and attached with addition funnel, was added a 3.0M MeMgBr (12 mL, 3.7 equiv) solution in Et2O. The flask was cooled to 0° C. prior to dropwise addition of ethyl 1-(4-bromophenyl)-2-(2-(2-fluorophenyl)propan-2-yl)-1H-imidazole-4-carboxylate (4.22 g, 9.78 mmol) in a solution of anhydrous dichloromethane (80 mL). The reaction solution was allowed to stir, warming to room temperature over 1 hr. The reaction solution was quenched by addition of aq NH4Cl. The mixture was poured to a reparatory funnel and the dichloromethane layer was partitioned, dried over Na2SO4, filtered, concentrated and chromatographed through a 40 g SiO2 column using a gradient of 100% Hx to 70% EtOAc to yield the title compound (3.19 g, 78% yield). LCMS (ES): m/z=417.3, 419.3 [M+H]+.

1. customTo a 250 mL round bottom flask, purged with dry N2
2. additionattached with addition funnel
3. temperaturewarming to room temperature over 1 hr
4. customThe reaction solution was quenched by addition of aq NH4Cl
5. additionThe mixture was poured to a reparatory funnel
6. customthe dichloromethane layer was partitioned
7. dry with materialdried over Na2SO4
8. filtrationfiltered
9. concentrationconcentrated
10. customchromatographed through a 40 g SiO2 column