Sodium Iodide → HCID 68872873, compound

Participants

Reaction Steps

A solution of 1.00 g (2.08 mmol) of 5-bromo-N-{1-methyl-1-[3-methyl-4-(3-oxomorpholin-4-yl)phenylcarbamoyl]ethyl}thiophene-2-carboxamide, 40 mg (0.208 mmol) of copper(I) iodide, 0.62 g (4.16 mmol) of sodium iodide and 0.044 ml (0.416 mmol) of N,N-dimethylethylene-1,2-diamine in 2.5 ml of dioxane is stirred at 100° C. for 20 h, cooled to room temperature, diluted with conc. ammonia and water and extracted with ethyl acetate. The combined organic phases are extracted with ethyl acetate, dried with sodium sulphate and concentrated in vac. The crude product (0.86 g) is directly reacted further. A suspension of the above crude product (0.86 g), 0.45 ml (3.26 mmol) of trimethylsilylacetylene and 0.68 ml (4.8 mmol) of triethylamine in 10 ml of acetonitrile/20 ml of THF is saturated with argon several times, and 67 mg (0.082 mmol) of PdCl2(dppf) and 15 mg (0.082 mmol) of copper(I) iodide are added. The initially reddish brown suspension becomes lemon-yellow after about 15 min. After stirring for 16 h, the mixture is diluted with ethyl acetate, washed with 5% ammonia solution, dried with sodium sulphate and concentrated in vac.

Provenance & Evidence