Cesium carbonate → 1-(4-Fluorophenyl)-6-(methyl(pyridin-3-ylmethyl)amino)-4-oxo-1,4-dihydroquinoline-3-carbonitrile

Participants

Reaction Conditions

Reaction Steps

Compound W (25 mg, 0.073 mmol, 1.0 eq), N-methyl-N-(3-pyridylmethyl)amine (17 mg, 0.15 mmol, 2.0 eq), cesium carbonate (33 mg, 0.10 mmol, 1.4 eq), tris(dibenzylideneacetone)dipalladium(0) (5.3 mg, 0.0058 mmol, 0.080 eq) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (5.1 mg, 0.0087 mmol, 0.12 eq) were dissolved in toluene (0.5 mL) in a sealed vial and heated at 110° C. overnight. The reaction was cooled, filtered over Celite® and washed with 5% methanol in DCM. The organics were concentrated and purified using reverse phase chromatography to afford 11.3 mg (40%) of the title compound as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 8.65 (s, 1H), 8.44-8.42 (m, 2H), 7.70-7.67 (m, 2H), 7.57 (dt, J=7.8, 1.8 Hz, 1H), 7.48 (t, J=8.7 Hz, 2H), 7.33-7.32 (m, 2H), 7.26 (dd, J=9.4, 3.1 Hz, 1H), 6.83 (d, J=9.3 Hz, 1H), 4.72 (s, 2H), 3.1 (s, 3H); ES-MS [M+1]+: 385.2.

Provenance & Evidence