Potassium Carbonate → Methyl 1-(6-methoxyquinolin-4-yl)-1H-indole-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

1.73 g (12.5 mmol) of potassium carbonate and 0.968 g (5 mmol) of 4-chloro-6-methoxyquinoline are added to 0.876 g (5 mmol) of 3-methoxycarbonyl-1H-indole in 20 cm3 of dimethylacetamide under an argon atmosphere. After stirring at a temperature in the region of 140° C. for 20 hours, the reaction mixture is cooled and diluted with 200 cm3 of ethyl acetate and 200 cm3 of water. The organic phase is separated off by settling and washed with three times 200 cm3 of water and 200 cm3 of saturated aqueous sodium chloride solution and then it is dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2.7 kPa). The residue obtained is purified by flash chromatography [eluent: cyclohexane/ethyl acetate (8/2 and then 7/3 by volume)]. Concentrating these fractions to dryness under reduced pressure (2.7 kPa) results in 0.7 g of 3-methoxycarbonyl-1-(6-methoxyquinol-4-yl)-1H-indole in the form of a white powder. Mass spectrum (EI): m/e 332 (M+•), m/e 301.

Provenance & Evidence