Propyne → (6-Phenyl-4-prop-1-ynylpyridin-3-yl)carbamic acid tert-butyl ester

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Reaction Steps

Propyne (0.60 mL, 11.4 mmol) was condensed in a pressure tube at −78° C. A solution of (4-iodo-6-phenylpyridin-3-yl)carbamic acid tert-butyl ester (900 mg, 2.27 mmol) in 2 mL of DMF, 6 mL of triethylamine, dichlorobis(triphenylphosphine)palladium (II) (80.2 mg, 0.114 mmol), and CuI (43.0 mg, 0.227 mmol) were added, the tube was sealed, and the mixture was stirred at room temperature overnight. The mixture was cooled to −78° C., the sealed tube was opened, and 20 mL of ethyl acetate and 10 mL of saturated aqueous ammonium chloride solution were added. The phases were separated and the aqueous layer was extracted with three 10 mL portions of ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude product was purified on SiO2 (0 to 40% ethyl acetate in hexanes, gradient) to give 670 mg of (6-phenyl-4-prop-1-ynylpyridin-3-yl)carbamic acid tert-butyl ester (96% yield).

Provenance & Evidence