Trifluoroacetic acid → HCID 59525921, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-methyl-2-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]propanenitrile and [6-(1-cyano-1-methylethyl)pyridin-3-yl]boronic acid as trifluoroacetic acid salts (260 mg, approx. 0.673 mmol combined), 5-bromo-2-nitrothiophene-3-carboxamide (169 mg, 0.673 mmol) (Intermediate 10 Step 4), and tetrakis(triphenylphosphine)palladium(0) (38.9 mg, 0.034 mmol) were dissolved in fully degassed tetrahydrofuran (2.7 ml) and fully degassed 2 M aqueous sodium carbonate (0.7 ml). The reaction was stirred at 70° C. for 4 hours. It was then allowed to cool to room temperature, taken up in ethyl acetate, and washed with water (2×) and brine (2×). The organic layer was dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was purified via reverse phase HPLC to yield the title compound.

Provenance & Evidence