Br[C:2]1[N:6]([CH3:7])[C:5]([CH3:8])=[N:4][CH:3]=1.C([Mg]Cl)(C)C.[Cl:14][C:15]1[CH:26]=[CH:25][C:18]([C:19](N(OC)C)=[O:20])=[CH:17][CH:16]=1>C1COCC1>[Cl:14][C:15]1[CH:26]=[CH:25][C:18]([C:19]([C:2]2[N:6]([CH3:7])[C:5]([CH3:8])=[N:4][CH:3]=2)=[O:20])=[CH:17][CH:16]=1To a 50-mL round-bottom flask containing a solution of 5-bromo-1,2-dimethyl-1H-imidazole (440 mg, 2.51 mmol, Intermediate 24, step a) and THF (20 mL) under nitrogen was added isopropylmagnesium chloride in THF (2.0 M, 1.2 mL, 2.4 mmol) dropwise. The mixture was stirred for 0.5 hours at room temperature, and a solution of 4-chloro-N-methoxy-N-methylbenzamide (500 mg, 2.50 mmol, Intermediate 18, step a) in THF (5 mL) was introduced. After stirring for 7.5 hours at room temperature, the reaction was quenched by addition of 10 mL of EtOH, and concentrated under vacuum. The residue was purified by flash column chromatography (silica gel, 50% EtOAc in petroleum, 0-10% MeOH in CH2Cl2) to give the title compound as a white solid.
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