Sodium hydride → 4-Bromo-2-((7-fluoro-3-methyl-2-(2-pyridinyl)-4-quinolinyl)oxy)benzonitrile

Participants

Reaction Steps

To a stirred solution of 7-fluoro-3-methyl-2-(pyridin-2-yl)quinolin-4-ol (130 mg, 0.51 mmol) in DMF (2.5 mL) was added sodium hydride (18.4 mg, 0.77 mmol). The reaction was stirred at rt for 20 min and then treated with 4-bromo-2-fluorobenzonitrile (102 mg, 0.51 mmol). The reaction was stirred at rt for 20 min and then at 110° C. for 12 h. After this time the reaction was cooled to rt and diluted with EtOAc (100 mL) and LiCl (1M aq. solution, 40 mL). The separated organic layer was dried over magnesium sulfate, filtered and evaporated in vacuo and the residue was purified by flash chromatography (hexanes:EtOAc, 1:0 to 2:1) to give 4-bromo-2-((7-fluoro-3-methyl-2-(2-pyridinyl)-4-quinolinyl)oxy)benzonitrile. 1H NMR (400 MHz, chloroform-d) δ ppm 8.75 (1H, d, J=5.1 Hz), 7.90-7.98 (2H, m), 7.77-7.89 (2H, m), 7.62 (1H, d, J=8.2 Hz), 7.29-7.45 (3H, m), 6.64 (1H, d, J=2.0 Hz), 2.41 (3H, s). Mass Spectrum (ESI) m/e=434.0 [(M+1) (79Br)] and 435.8 [(M+1) (81Br)].

Provenance & Evidence