C(=O)([O-])[O-].[Cs+].[Cs+].Cl.Cl.[NH:9]1[CH2:12][CH:11]([C:13]2[NH:17][C:16]3[CH:18]=[CH:19][C:20]([CH3:22])=[CH:21][C:15]=3[N:14]=2)[CH2:10]1.[Cl:23][C:24]1[C:29](Cl)=[N:28][CH:27]=[CH:26][N:25]=1>CN1C(=O)CCC1>[Cl:23][C:24]1[C:29]([N:9]2[CH2:12][CH:11]([C:13]3[NH:17][C:16]4[CH:18]=[CH:19][C:20]([CH3:22])=[CH:21][C:15]=4[N:14]=3)[CH2:10]2)=[N:28][CH:27]=[CH:26][N:25]=1To a mixture of cesium carbonate (4.44 g, 13.6 mmol) and 2-(azetidin-3-yl)-5-methyl-1H-benzo[d]imidazole dihydrochloride (1.05 g, 4.04 mmol) was added NMP (6 mL) and 2,3-dichloropyrazine (1.0 mL, 9.6 mmol). The reaction mixture was degassed and heated to 100° C. for 30 min. The reaction was diluted with EtOAc. The organic phase was washed with water (2×), brine (1×), dried over MgSO4, filtered, and concentrated. Purification by flash column chromatography on silica gel (50% to 100% EtOAc in hexanes) gave 2-(1-(3-chloropyrazin-2-yl)azetidin-3-yl)-5-methyl-1H-benzo[d]imidazole (0.532 g, 1.78 mmol, 44% yield) as an orange solid.
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