C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[N:13]=[C:12]2[N:14]=[CH:15][NH:16][C:11]2=[C:10]([Cl:17])[CH:9]=1.Br[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[C:21]=1[CH3:30]>CN(C)C=O>[Cl:7][C:8]1[N:13]=[C:12]2[N:14]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:27])([F:28])[F:29])[C:21]=3[CH3:30])[CH:15]=[N:16][C:11]2=[C:10]([Cl:17])[CH:9]=1Potassium carbonate (1139 mg, 8.24 mmol) was added to a solution of 5,7-dichloro-1H-imidazo[4,5-b]pyridine (500 mg, 2.66 mmol) in N,N-Dimethylformamide (DMF) (8.5 mL) and the mixture was stirred for 25 min. 1-(bromomethyl)-2-methyl-3-(trifluoromethyl)benzene (942 mg, 3.72 mmol) was then added and the reaction mixture was stirred at rt overnight. The mixture was partitioned between water and EtOAc. The aqueous layer was extracted with additional EtOAc (2×25 mL). The combined organic extracts were washed with brine, dried over Na2SO4 and evaporated. The residue was purified on silica gel (15 to 30% EtOAc in hexanes) to give 5,7-dichloro-3-{[2-methyl-3-(trifluoromethyl)phenyl]methyl}-3H-imidazo[4,5-b]pyridine (456 mg, 1.266 mmol, 47.6% yield) as an off-white powder. MS (ES+) m/e 359 (MH+) 1H NMR (400 MHz, DMSO-d6) δ ppm 8.64 (s, 1H), 7.68 (s, 1H), 7.66 (d, J=8.08 Hz, 1H), 7.33 (t, J=7.71 Hz, 1H), 7.07 (d, J=7.83 Hz, 1H), 5.62 (s, 2H) (Ar—CH3 hidden under DMSO peak).
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