Water → 7-(4-Methanesulfonyl-phenyl)-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine

Participants

Reaction Conditions

Reaction Steps

Into a 30 ml, vial, Palladium Acetate (0.11 g, 0.00049 mol) and Triphenylphosphine (0.32 g, 0.0012 mol) were added and purged under an atmosphere of Nitrogen for 5 minutes 1,4-Dioxane (10.8 mL, 0.138 mol) was added and stirred for 10 minutes. 7-Bromo-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine (0.600 g, 0.00246 mol), (4-Methylsulfonylphenyl)boronic acid (0.983 g, 0.00492 mol), N,N-Dimethylformamide (23.7 mL, 0.306 mol) and 1.50 M of Sodium carbonate in Water (4.92 mL, 0.00737 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 hexane and EtOAc as eluant (0 to 100% EtOAc). The collected fraction afforded 7-(4-Methanesulfonyl-phenyl)-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine a yellow solid (0.63 g, 83%). NMR 1H (DSMO-d6)-9.09 (s, 1H), 8.51 (d, 2H, J=8.48 Hz), 8.05 (d, 2H, J=8.49 Hz), 7.58 (d, 1H, J=4.84 Hz), 7.15 (d, 1H, J=4.84 Hz), 3.27 (s, 3H), 2.62 (s, 3H).

Provenance & Evidence