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[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][CH:21]=1>CN(C)C=O>[Cl:7][C:8]1[N:13]=[C:12]2[N:14]([CH2:19][C:20]3[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[CH:23]=[CH:22][CH:21]=3)[CH:15]=[N:16][C:11]2=[C:10]([Cl:17])[CH:9]=1Potassium carbonate (798 mg, 5.77 mmol) was added to a solution of 5,7-dichloro-1H-imidazo[4,5-b]pyridine (350 mg, 1.862 mmol) (5,7-dichloro-3H-imidazo[4,5-b]pyridine, obtained as described in example 1) in N,N-Dimethylformamide (DMF) (6.5 mL) and the mixture was stirred for 25 min. 1-(bromomethyl)naphthalene (576 mg, 2.61 mmol) was then added and the reaction mixture was stirred at rt overnight. The mixture was poured onto water and the precipitate formed was collected by filtration. The residue was purified on silica gel (15 to 30% EtOAc in hexanes) to give 5,7-dichloro-3-(1-naphthalenylmethyl)-3H-imidazo[4,5-b]pyridine (160 mg, 0.488 mmol, 26.2% yield) as a light yellow powder. MS (ES+) m/e 328 (MH+); 1H NMR (400 MHz, DMSO-d6) δ ppm 8.67 (s, 1H), 8.25 (d, J=8.08 Hz, 1H), 7.97-8.03 (m, 1H), 7.92 (d, J=8.34 Hz, 1H), 7.66-7.70 (m, 1H), 7.56-7.66 (m, 2H), 7.41-7.49 (m, 1H), 7.11 (d, J=6.32 Hz, 1H), 6.00 (s, 2H)
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