Water → 3-[3-(2-Methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenyl]-propionitrile

Participants

Reaction Steps

Into a 8-dram vial, Palladium Acetate (0.057 g, 0.26 mmol) and Triphenylphosphine (0.19 g, 0.00072 mol) were added. The mixture was purged under an atmosphere of Nitrogen for 10 minutes. 1,4-Dioxane (19.4 mL) was added and stirred for 10 minutes at room temperature. 7-Bromo-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine (0.623 g, 2.55 mmol), 3-[3-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propionitrile (1.31 g, 5.10 mmol), N,N-Dimethylformamide (39 mL), and 1.50 M of Sodium carbonate in Water (15.3 mL, 0.0230 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 product was isolated via column chromatography with DCM and Methanol as eluant (1 to 8% MeOH). The collected fractions afforded a solid. The solid was triturated with Et2O and filtered to give 3-[3-(2-Methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenyl]-propionitrile as a yellow solid (560 mg, 64%).

Provenance & Evidence