3-Fluoroaniline → 6-Fluoro-4-(3-fluorophenylamino)-1,7-naphthyridine-3-carbonitrile

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Reaction Steps

Following the procedure described above in Example 13, 4-chloro-6-fluoro-1,7-naphthyridine-3-carbonitrile (0.300 g, 1.45 mmol) was reacted with 3-fluoroaniline (0.15 mL, 0.18 g, 1.6 mmol). The crude product was purified by flash chromatography over silica gel (10% EtOAc in CH2Cl2) to give pure 6-fluoro-4-(3-fluorophenylamino)-1,7-naphthyridine-3-carbonitrile (0.185 g, 45% yield): 1H NMR (400 MHz, DMSO-D6) δ 7.16 (td, J=8.5, 2.7 Hz, 1 H) 7.22 (ddd, J8.0, 2.0, 0.9 Hz, 1 H) 7.27 (dt, J=10.2, 2.2 Hz, 1 H) 7.43-7.53 (m, 1 H) 8.17 (s, 1 H) 8.72 (s, 1 H) 9.10 (s, 1 H) 10.16 (s, 1 H).

Provenance & Evidence