[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[N:10]=2)[CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Br[C:42]1[CH:47]=[CH:46][CH:45]=[C:44]([F:48])[CH:43]=1>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:42]3[CH:47]=[CH:46][CH:45]=[C:44]([F:48])[CH:43]=3)=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[N:10]=2)[CH:7]=1A solution of ethyl 6-chloroimidazo[1,2-a]pyridine-2-carboxylate (0.8 g, 3.6 mmol), cesium carbonate (1.3 g, 3.9 mmol), palladium acetate (64 mg, 0.29 mmol), and triphenylphosphine (0.15 g, 0.57 mmol) in 1,4-dioxane (43 mL) was treated with 1-bromo-3-fluorobenzene (0.54 mL, 4.8 mmol), degassed with nitrogen, and heated in the microwave at 150° C. for 30 min. The reaction mixture was filtered over celite and the filtrate was concentrated to give a crude residue. This material was purified by flash column chromatography to give the desired product (1.2 g, 94%). LCMS for C16H13ClFN2O2 (M+H)+: m/z=319.1.
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