Into a 30 mL vial, Palladium Acetate (0.010 g, 0.000046 mol) and Triphenylphosphine (0.030 g, 0.00011 mol) were added and purged under an atmosphere of Nitrogen for 5 minutes 1,4-Dioxane (1.00 mL, 0.0128 mol) was added and stirred for 10 minutes. (7-Bromo-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-[2-methoxy-4-(4-methyl-piperazin-1-yl)-phenyl]-amine (0.0952 g, 0.000228 mol), 2-methoxybenzeneboronic acid (0.0694 g, 0.000456 mol), N,N-Dimethylformamide (2.20 mL, 0.0284 mol) and 1.50 M of Sodium carbonate in Water (1.00 mL, 0.00150 mol) were added, respectively. The reaction mixture was heated at 80° C. overnight. The solvent was removed under vacuum. The solid was washed with DCM. The organic was removed under vacuum. The reaction was purified via ISCO column chromatography with DCM and methanol as eluant (0 to 10% methanol). The collected fraction afforded a solid. The solid was washed with 10% Et2O/hexane to give [2-Methoxy-4-(4-methyl-piperazin-1-yl)-phenyl]-[7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-amine a yellow solid (38 mg, 37%). LCMS (E/I+) 445.19 (M+H). NMR 1H (DSMO-d6)-8.88 (s, 1H), 7.83 (t, 2H, J=8.76 Hz), 7.48 (s, 1H), 7.43 (t, 1H, J=7.16 Hz), 7.19 (d, 1H, J=8.36 Hz), 7.08 (t, 1H, J=7.52 Hz), 6.94 (d, 1H, J=4.68 Hz), 6.90 (d, 1H, J=4.60 Hz), 6.63 (s, 1H), 6.35 (d, 1H, J=9.04 Hz), 3.84 (s, 3H), 3.78 (s, 3H), 3.05-3.16 (bm, 4H), 2.46 (bs, 4H), 2.23 (s, 3H).
