Ethanol → HCID 66710816, compound

Participants

Reaction Steps

7-(5-Chloro-2-methoxy-phenyl)-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine Palladium Acetate (0.37 g, 0.0016 mol) and Triphenylphosphine (0.54 g, 0.0020 mol) were dissolved in Tetrahydrofuran (25 mL, 0.31 mol) and the mixture was allowed to stir at room temperature for 10 minutes. 7-Bromo-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine (2.00 g, 0.00819 mol) was then added and the reaction was again allowed to stir for 10 minutes. 5-Chloro-2-methoxyphenyl boronic acid (3.05 g, 0.0164 mol) was added followed by 0.9 M of Sodium carbonate in water (20 mL, 0.02 mol) and Ethanol (25 mL, 0.43 mol). The reaction mixture was then heated at 80° C. and was allowed to stir overnight. The reaction mixture was then poured over saturated sodium chloride, and organics were extracted with ethyl acetate/dichloromethane. Combined organics were dried over sodium sulfate, filtered and reduced en vacuo. The crude mixture was purified by Isco flash column chromatography (Hexane/Ethyl Acetate). Combined fractions were reduced en vacuo to afford 1.16 g of 7-(5-Chloro-2-methoxy-phenyl)-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine as a yellow solid.

Provenance & Evidence