CC1C(C#N)=[CH:4][C:5]2[N:9]=[CH:8][N:7]([CH:10]3[CH2:15][CH2:14][CH2:13][CH2:12][O:11]3)C=2C=1.[CH3:19][Mg+].[Br-].[C:22]([OH:34])(=O)[CH2:23][C:24]([CH2:29][C:30](O)=O)([C:26](O)=O)O>C1COCC1>[CH3:26][C:24]1[C:23]([C:22](=[O:34])[CH3:19])=[CH:4][C:5]2[N:9]=[CH:8][N:7]([CH:10]3[CH2:15][CH2:14][CH2:13][CH2:12][O:11]3)[C:30]=2[CH:29]=1To a solution of 6-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazole-5-carbonitrile (1.1 g, 4.6 mmol) in anhydrous THF (20 mL) under nitrogen at 0° C. was dropped a solution of CH3MgBr in THF (8 mL, 24 mmol) at a rate that the internal reaction temperature remained below 10° C. After the addition, the reaction mixture was stirred at RT overnight. The mixture was slowly poured into ice-water (20 mL) and stirred at RT for 0.5 h. The solution's pH was adjusted to 5.0˜6.0 by using citric acid, and mixture was extracted with EtOAc (20 mL×3). The combined organic layers were washed with brine, dried (Na2SO4), and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with petroleum ether/EtOAc (1:1) to afford 1-(6-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-5-yl)ethanone as a yellow solid (1.1 g, 90.1%). MS (ESI): m/z=259.2 [M+1]+.
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