Trifluoroacetic acid → 2-(6-Amino-2,7-naphthyridin-1-yl)isoindoline-1,3-dione

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Reaction Conditions

Reaction Steps

A mixture of 4-6 (3.94 g, 7.43 mmol), trifluoroacetic acid (30.0 mL, 392 mmol), and dichloromethane (30.0 mL) was stirred at 40° C. for 19 hours under an atmosphere of nitrogen gas and concentrated under reduced pressure. To the resulting residue was added saturated aqueous NaHCO3 (300 mL) and hexane/dichloromethane (5:1) (150 mL) at ambient temperature. The resulting mixture was stirred vigorously at ambient temperature for 30 minutes. The precipitated solid was filtered, washed with water (60 mL) and hexane/dichloromethane (5:1) (60 mL), and dried under high vacuum to give 2.08 g (96%) of 4-7 as a pale yellow solid: 1H NMR (400 MHz, DMSO-d6) δ 9.04 (1H, br s), 8.28 (1H, d, J=6.0 Hz), 8.05 (2H, m), 7.97 (2H, m), 7.55 (1H, br d, J=6.0 Hz), 6.78 (2H, br s), 6.63 (1H, br s); ESI-MS m/z 291 [C16H10N4O2+H]+.

Provenance & Evidence