Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([F:12])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[N:13]1[N:14]=[CH:15][N:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=12.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[N:13]1[N:14]=[C:15]([C:2]2[CH:11]=[CH:10][C:9]3[C:4](=[C:5]([F:12])[CH:6]=[CH:7][CH:8]=3)[N:3]=2)[N:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=122-Chloro-8-fluoroquinoline (0.75 g, 4.13 mmol) was combined with [1,2,4]triazolo[4,3-a]pyridine (0.541 g, 4.54 mmol), micronized Cs2CO3 (2.69 g, 8.26 mmol), and PdCl2(PPh3)2 (0.290 g, 0.413 mmol) then the mixture was slurried in dioxane (20 mL). The reaction was deoxygenated with argon and heated to reflux for 20 hours, then cooled, diluted with CHCl3 and filtered through a pad of Celite®. The filtrate was concentrated onto Na2SO4 powder (15 g) and the mixture was chromatographed on SiO2 eluting with a stepped gradient of 0-2% MeOH/ethyl acetate. The desired product was isolated as a cream-colored solid (1.12 g). MS APCI (+) m/z 265.3 (M+1) detected.
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