C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O1CCOCC1.Br[C:27]1[N:35]2[C:30]([CH:31]=[N:32][C:33]([S:36]([CH3:38])=[O:37])=[N:34]2)=[CH:29][CH:28]=1.[N:39]1[CH:44]=[CH:43][CH:42]=[C:41](B(O)O)[CH:40]=1.C(=O)([O-])[O-].[Na+].[Na+].O.C(O)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C=O)C>[CH3:38][S:36]([C:33]1[N:32]=[CH:31][C:30]2=[CH:29][CH:28]=[C:27]([C:41]3[CH:40]=[N:39][CH:44]=[CH:43][CH:42]=3)[N:35]2[N:34]=1)=[O:37]Into a round bottom flask, Palladium Acetate (0.052 g, 0.00023 mol) and Triphenylphosphine (0.076 g, 0.00029 mol) were dissolved in dioxane (3.5 mL, 0.043 mol) and the mixture was allowed to stir at room temperature for 10 minutes. DMF (5 mL), 7-Bromo-2-methanesulfinyl-pyrrolo[2,1-f][1,2,4]triazine (0.300 g, 0.00115 mol) was then added and the reaction was again allowed to stir for 10 minutes. [B] 3-Pyridylboronic acid (0.284 g, 0.00231 mol) was added followed by 0.9 M of Sodium carbonate in water (1 mL, 0.001 mol) and Ethanol (3.5 mL, 0.060 mol). The reaction mixture was then heated at 80° C. overnight. The reaction was partitioned with water and DCM. The organic was separated, washed with Brine and dried over sodium sulfate. The solid was filtered and washed. The solvent was removed under vacuum. The reaction mixture was purified by ISCO column chromatography with DCM and methanol as eluant (0 to 10%). The collected fractions afforded 2-Methanesulfinyl-7-pyridin-3-yl-pyrrolo[2,1-f][1,2,4]triazine as a yellow solid (0.19 g, 61%). LCMS (E/I+) 259.8 (M+H)
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