Trifluoroacetic acid → 6-Amino-4-(3-bromo-phenylamino)-[1,7]naphthyridine-3-carbonitrile

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Reaction Steps

To 1.3 g of 4-(3-bromo-phenylamino)-6-fluoro-[1,7]naphthyridine-3-carbonitrile in 20 mL of absolute ethanol was added 5 ml of 4-methoxy-benzylamine. The reaction was refluxed for six days, stripped of solvents, and passed through a plug of silica gel with 5% methanol/chloroform. This crude product was dissolved in 10 mL of chloroform containing 5% anisole and 10 mL of trifluoroacetic acid was added. After stirring under an inert atmosphere for 20 hours, 10 mL of toluene was added and the solvents stripped on a rotary evaporator. The product was purified by flash chromatography with a gradient of 0-10% methanol/chloroform. The solid was extracted with hot, 5% methanol/isopropyl ether and then cooled, filtered, and dried to give 250 mg of 6-amino-4-(3-bromo-phenylamino)-[1,7]naphthyridine-3-carbonitrile as an off-white solid. mass spectrum (m/e): M+H 306.2.

Provenance & Evidence