Dodecane → Methyl 1-(isoquinolin-3-yl)-1H-indole-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

25 cm3 of 1,4-dioxane, 0.256 cm3 of n-dodecane, 1.25 g (4.9 mmol) of 3-iodoisoquinoline and 0.582 cm3 (4.85 mmol) of trans-1,2-cyclohexanediamine are added at a temperature in the region of 22° C. under an argon atmosphere to 0.850 g (4.85 mmol) of 3-methoxycarbonyl-1H-indole, 2.2 g (10.36 mmol) of potassium orthophosphate and 0.085 g (0.45 mmol) of copper iodide. After stirring at a temperature in the region of 100° C. for 17 hours, the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa). The residue is diluted with 100 cm3 of dichloromethane, the suspension obtained is filtered and the filtrate is concentrated to dryness under reduced pressure (2.7 kPa) to give 2.3 g of a brown oil which is purified by flash chromatography [eluent: cyclohexane/ethyl acetate (85/15 by volume)]. After concentrating the fractions under reduced pressure, 1.1 g of 3-methoxycarbonyl-1-(isoquinol-3-yl)-1H-indole are obtained in the form of a white solid. Mass spectrum (EI): El: m/e 302 (M+·), m/e 271.

Provenance & Evidence