Sodium Carbonate → (S)-2-(1-((5-(4-Amino-2-methoxyphenyl)-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 (400 mg, 0.67 mmol) was dissolved in 6 mL N,N-dimethylformamide. 3-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (490 mg, 1.77 mmol, 90% purity), 2M sodium carbonate aqueous solution (0.81 mL, 1.62 mmols) and tetrakis(triphenylphosphine)palladium(0) (233 mg, 0.2 mmol) were added under argon atmosphere and the reaction mixture was stirred at 90° C. for 5 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 100%, hexane-ethyl acetate) to give 383 mg (81% yield) of the title compound.

Provenance & Evidence