Isobutylamine → 7-bromo-N-(2-methylpropyl)-3-nitro[1,5]naphthyridin-4-amine

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Reaction Steps

Isobutylamine (16.2 mL, 163 mmol) was added dropwise to a 0° C. solution of 7-bromo-4-chloro-3-nitro[1,5]naphthyridine (approximately 74.1 mmol) in dichloromethane (350 mL). The reaction mixture was allowed to stir and warm to room temperature for 3 hours, then was diluted with dichloromethane (50 mL) and washed with saturated aqueous sodium bicarbonate (300 mL). The aqueous layer was back-extracted with dichloromethane (2×75 mL). The organic layers were combined, dried over magnesium sulfate, filtered, and concentrated to afford 23.06 g of 7-bromo-N-(2-methylpropyl)-3-nitro[1,5]naphthyridin-4-amine as a yellow solid.

Provenance & Evidence