Reaction Steps
1155h. Into a 8-dram vial, Palladium Acetate (0.0059 g, 0.000026 mol) and Triphenylphosphine (0.019 g, 0.000074 mol) were added. The mixture was purged under an atmosphere of Nitrogen for 10 minutes. 1,4-Dioxane (2.00 mL, 0.0256 mol) was added and stirred for 10 minutes at room temperature. (6-Bromo-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-[4-(4-methyl-piperazin-1-yl)-phenyl]-amine (0.102 g, 0.000264 mol), [2-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenoxy]-acetonitrile (0.137 g, 0.000527 mol), N,N-Dimethylformamide (4.0 mL, 0.052 mol), and 1.50 M of Sodium carbonate in Water (1.58 mL, 0.00237 mol) were added. The reaction was heated at 90° C. for 3 hours. The reaction was partitioned with water and EtOAc. The organic was separated, washed with Brine, and dried over magnesium sulfate. The solid was filtered and washed with EtOAc. The solvent was removed under vacuum. The reaction mixture was purified via HPLC reverse phase chromatography with 0.1% TFA in Water and 0.1% TFA in ACN. The collected fractions afforded a solid. The solid was triturated with Et2O and filtered to give (2-{2-[4-(4-Methyl-piperazin-1-yl)-phenylamino]-pyrrolo[2,1-f][1,2,4]triazin-6-yl}-phenoxy)-acetonitrile a yellow solid (5 mg, 3%). LCMS (E/I+) 440.18 (M+H). NMR 1H (DMSO-d6)-9.57 (s, 1H), 9.29 (s, 1H), 8.93 (s, 1H), 8.18 (s, 1H), 7.81 (d, 1H, J=7.81 Hz), 7.69 (d, 2H, J=8.19 Hz), 7.34 (t, 1H, J=7.80 Hz), 7.26 (d, 1H, J=7.80 Hz), 7.21 (s, 1H), 7.14 (t, 1H, J=7.02 Hz), 7.00 (d, 2H, J=8.19 Hz), 5.32 (s, 2H), 3.75 (d, 2H, J=12.58 Hz), 3.485-3.59 (m, 2H), 3.09-3.24 (m, 2H), 2.80-2.97 (m, 5H).
