Water → Methyl 5-fluoro-1-(quinolin-4-yl)-1H-indole-3-carboxylate

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Reaction Conditions

Reaction Steps

0.384 g (12 mmol) of sodium hydride, at 75% by mass in liquid petroleum jelly, is added at a temperature in the region of 20° C. under an argon atmosphere to a solution of 2.26 g.(11.7 mmol) of 5-fluoro-3-methoxycarbonyl-1H-indole in 60 cm3 of dimethylformamide. After stirring at a temperature in the region of 40° C. for 0.5 hour, 1.98 g (12 mmol) of 4-chloroquinoline are added. After stirring at a temperature in the region of 120° C. for 6 hours, the reaction mixture is poured into 200 cm3 of water and extracted with 200 cm3 of ethyl acetate. The organic phase is washed with 3 times 100 cm3 of water and is then dried over anhydrous magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2.7 kPa) to give 3.5 g of a brown solid which is purified by silica gel chromatography (eluent: dichloromethane). After concentrating the fractions under reduced pressure, 1.6 g of 5-fluoro-3-methoxycarbonyl-1-(quinol-4-yl)-1H-indole are obtained in the form of a beige-coloured solid melting at 172° C.

Provenance & Evidence