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

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Reaction Steps

7-(2-Methoxy-phenyl)-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]: Into a 200 mL round bottom flask, Palladium Acetate (0.20 g, 0.00088 mol) and Triphenylphosphine (0.65 g, 0.0025 mol) were added. The mixture was purged under an atmosphere of Nitrogen for 10 minutes. 1,4-Dioxane (66.8 mL, 0.856 mol) was added and stirred for 10 minutes at room temperature. 7-Bromo-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine (2.150 g, 0.008807 mol), 2-methoxybenzeneboronic acid (2.68 g, 0.0176 mol), N,N-Dimethylformamide (130 mL, 1.7 mol), and 1.50 M of Sodium carbonate in Water (52.8 mL, 0.0793 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 desired product was purified via ISCO column chromatography with DCM and methanol as eluant (0 to 3% methanol). The collected fractions afforded 7-(2-Methoxy-phenyl)-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine as a yellow solid (1.85 g, 78%). NMR 1H (DSMO-d6)-8.89 (s, 1H), 7.81 (dd, 1H, JJ=2.74, 6.01 Hz), 7.42 (td, 1H, JJ=1.68, 6.92 Hz), 7.07-7.25 (m, 4H), 3.81 (s, 3H), 2.43 (s, 3H)

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