Dodecane → HCID 21110086, compound

Participants

Reaction Steps

1.76 g (10 mmol) of methyl 1H-pyrrolo[2,3-b]pyridine-3-carboxylate, 2.66 g (13 mmol) of 4-iodopyridine, 0.19 g (1 mmol) of copper(1) iodide, 4.46 g (21 mmol) of tripotassium phosphate, 1.2 cm3 of a trans-1,2-cyclohexanediamine (10 mmol) and 0.5 cm3 of n-dodecane were added to 100 cm3 of dioxane under an argon atmosphere at a temperature in the region of 20° C. The mixture was heated at reflux of the solvent for 20 h and then it was rapidly added to a mixture of 300 cm3 of ethyl acetate and 300 cm3 of water. The organic phase was separated by settling, washed 3 times with 300 cm3 of water and then 300 cm3 of saturated aqueous sodium chloride solution, dried over magnesium sulfate and then concentrated to dryness under reduced pressure (2.7 kPa). The residue was purified by flash chromatography on a column of silica gel (0.04–0.06 mm), elution being carried out with a cyclohexane/ethyl acetate (50/50 by volume) mixture. The fractions comprising the expected product were combined and concentrated to dryness under reduced pressure (2.7 kPa) and the residue was triturated in 30 cm3 of diisopropyl ether, filtered off and then dried under a hood. 1.7 g of methyl 1-(pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylate were thus obtained in the form of a white powder.

Provenance & Evidence