Sodium Carbonate → (S)-2-(1-((5-(3-Fluoro-5-hydroxyphenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one

Participants

Reaction Conditions

Reaction Steps

(S)-2-(1-((5-Bromo-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (110 mg, 0.19 mmol) was dissolved in 1.32 mL 1,2-dimethoxyethane and 0.33 mL water. (3-Fluoro-5-hydroxyphenyl)boronic acid (69 mg, 0.44 mmol), sodium carbonate (47 mg, 0.44 mmols) and bis(triphenylphosphine)palladium(II) dichloride (13 mg, 0.02 mmol) were added under argon atmosphere and the mixture was heated at 70° C. for 2 h. The reaction mixture was poured into a saturated ammonium chloride solution and extracted twice with water. The organics were washed with water, brine, dried over sodium sulphate, filtered and evaporated under reduced pressure. The residue was purified using SP1® Purification System (0% to 50%, hexane-ethyl acetate) to give 61 mg (53% yield) of the title compound. Purity 99%.

Provenance & Evidence