Ethylene Glycol → [7-(2-Methoxy-phenylsulfanyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-[4-(4-methyl-piperazin-1-yl)-phenyl]-amine

Participants

Reaction Conditions

Reaction Steps

Into a sealed tube was added (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), Sodium tert-butoxide (238 mg, 2.48 mmol), Copper(I) iodide (16 mg, 0.083 mmol), 1,2-Ethanediol (92.6 uL, 1.66 mmol), N,N-Dimethylformamide (12 mL, 150 mmol), and finally 2-Methoxy-benzenethiol (0.174 g, 1.24 mmol). The reaction was heated at 120° C. overnight. The reaction was partitioned with DCM and water. The organic was separated, washed with Brine, and dried over magnesium sulfate. The solid was filtered and washed with DCM. The solvent was removed under vacuum. The product was isolated via ISCO column chromatography with DCM and methanol as eluant (0 to 10% methanol). The collected fractions afforded [7-(2-Methoxy-phenylsulfanyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-[4-(4-methyl-piperazin-1-yl)-phenyl]-amine an orange solid (9 mg, 2.5%). MP 171-172° C. LCMS (E/I+) 447.24 (M+H). NMR 1H (DSMO-d6)-9.27 (s, 1H), 8.97 (s, 1H), 7.35 (d, 2H, J=9.00 Hz), 7.08-7.20 (m, 2H), 6.97 (d, 1H, J=4.68 Hz), 6.92 (d, 1H, J=4.57 Hz), 6.75 (t, 1H, J=6.72 Hz), 6.68 (d, 2H, J=9.08 Hz), 6.36 (dd, 1H, JJ=1.40, 6.41 Hz), 3.91 (s, 3H), 3.01 (t, 4H, J=4.72 Hz), 2.43 (t, 4H, J=4.68 Hz), 2.21 (s, 3H).

Provenance & Evidence