Water → HCID 46851380, compound

Participants

Reaction Steps

Into a 8-dram vial, Palladium Acetate (0.00988 g, 0.0440 mmol), Triphenylphosphine (0.0338 g, 0.129 mmol) and 1,4-Dioxane (2 mL) were added and stirred at room temperature for 10 minutes. (7-Bromo-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-[4-(4-methyl-piperazin-1-yl)-phenyl]-amine (0.320 g, 0.826 mmol), 2-Formylfuran-5-boronic acid (0.2312 g, 1.652 mmol), N,N-Dimethylformamide (2 mL) and 1.50 M of Sodium carbonate in Water (6 mL, 10 mmol) were added. The reaction mixture was heated at 90° C. overnight. The reaction was cooled to room temperature. Solvent was removed under vacuum to give a yellow solid. The resulting solid was partitioned with water and DCM. The organic was separated, washed with Brine and dried over Na2SO4. The solid was filtered and washed with DCM. The solvent was removed under vacuum. The reaction mixture was purified via ISCO column chromatography with DCM and methanol as eluant (5 to 25% methanol). The collected fractions afforded 5-{2-[4-(4-Methyl-piperazin-1-yl)-phenylamino]-pyrrolo[2,1-f][1,2,4]triazin-7-yl}-furan-2-carbaldehyde as a yellow solid (110 mg, 33%). LCMS (E/I+) 403.19 (M+H). NMR 1H (DMSO-d6)-963 (s, 1H), 9.40 (s, 1H), 9.04 (s, 1H), 7.78 (d, 1H, J=3.07 Hz), 7.62 (d, 2H, J=9.05 Hz), 7.45 (d, 1H, J=3.77 Hz), 7.21 (d, 1H, J=4.90 Hz), 7.01 (d, 2H, J=9.05 Hz), 6.97 (d, 1H, J=4.90 Hz), 3.11 (t, 4H, J=4.91 Hz), 2.47 (t, 4H, J=4.91 Hz), 2.23 (s, 3H).

Provenance & Evidence