6-Chloro-4-phenylamino-pyridine-3-carbaldehyde → 3-(3-amino-4-fluorophenyl)-7-chloro-1-phenyl-1,6-naphthyridin-2(1H)-one

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Reaction Steps

A mixture of 6-Chloro-4-(phenylamino)nicotinaldehyde (3 g, 13 mmol), ethyl 2-(3-amino-4-fluorophenyl)acetate (2.6 g, 13 mmol), and KF/Al2O3 (40 wt %, 10 g, 69 mmol) in DMAc (30 mL) was stirred at RT for 2 hours. The solids were removed by filtration and the filtrate was concentrated in vacuo. Recrystallization (EtOAc) provided 3-(3-amino-4-fluorophenyl)-7-chloro-1-phenyl-1,6-naphthyridin-2(1H)-one (2.6 g, 55% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.81 (s, 1 H), 8.20 (s, 1 H), 7.62-7.56 (m, 3 H), 7.40 (d, J=7.2 Hz, 2 H), 7.13 (d, J=7.6 Hz, 1 H), 7.02 (t, J=10.0 Hz, 1 H), 6.82 (m, 1 H), 6.26 (s, 1 H), 5.19 (s, 2 H); MS (ESI) m/z: 366.2 [M+H]+.

Provenance & Evidence