3-(Azidomethyl)-8-chloro-2-(5-fluoro-2-methoxyphenyl)quinoline → (8-Chloro-2-(5-fluoro-2-methoxyphenyl)quinoline-3-yl)methanamine

Participants

Reaction Steps

To a stirred solution of 3-(azidomethyl)-8-chloro-2-(5-fluoro-2-methoxyphenyl)-quinoline (210.7 mg, 615 μmol) in THF 5 mL and MeOH 12 mL was added palladium, 10 wt. % on activated carbon (0.329 mmol) and placed under a medium balloon containing H2. The reaction was complete after 2 h, it was filtered (Celite™) and solvents removed. Chromatography: Gradient 89:9:1. 1H NMR (400 MHz, choroform-d) δ ppm 8.30 (1H, s), 7.80 (2H, ddd, J=7.9, 6.5, 1.3 Hz), 7.49-7.50 (1H, m), 7.47 (1H, dd), 7.09-7.18 (2H, m), 6.93 (1H, dd, J=8.9, 4.2 Hz), 3.89 (2H, br. s.), 3.74 (3H, s) Mass Spectrum (ESI) m/e=317.0 (M+1).

Provenance & Evidence