4,4,5,5-Tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane → 7-(Prop-1-en-2-yl)pyrrolo[2,1-f][1,2,4]triazin-4-amine

Participants

Reaction Conditions

Reaction Steps

Under an argon atmosphere, 7-bromopyrrolo[2,1-f][1,2,4]triazin-4-amine (426 mg, 2 mmol) and 4,4,5,5-tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane (420 mg, 2.5 mmol) were dissolved in a mixture of 1,2-dimethoxyethane (10 mL) and aqueous sodium carbonate solution (2 M, 4 mL). The reaction mixture was degassed, and 1,1′-bis(diphenylphosphino)ferrocenepalladium(II) chloride (73 mg, 0.1 mmol) was added. After stirring at 90° C. overnight, the reaction mixture was diluted with ethyl acetate (40 mL), water (10 mL) was added, and the layers were separated. The aqueous layer was extracted with ethyl acetate (2×40 mL), and the combined organic layers were dried over sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography (puriFlash, Interchim, cyclohexane/ethyl acetate 1:1 to 100% ethyl acetate gradient) to yield the title product as a slightly yellow solid. Yield: 304 mg (81% of th.).

Provenance & Evidence