Cesium carbonate → Ethyl 1-(4-fluorophenyl)-6-(methyl(pyridin-3-ylmethyl)amino)-4-oxo-1,4-dihydroquinoline-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

Compound D (75 mg, 0.19 mmol, 1.0 eq), N-methyl-N-(3-pyridylmethyl)amine (47 mg, 0.38 mmol, 2.0 eq), cesium carbonate (88 mg, 0.27 mmol, 1.4 eq), tris(dibenzylideneacetone)dipalladium(0) (14 mg, 0.015 mmol, 0.080 eq) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (13 mg, 0.023 mmol, 0.12 eq) were dissolved in toluene (1.9 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 27 mg (33%) of the title compound as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 8.44 (s, 2H), 8.28 (s, 1H), 7.68 (dd, J=6.9, 4.9 Hz, 2H), 7.58 (d, J=7.8 Hz, 1H), 7.47 (t, J=8.7 Hz, 2H), 7.40 (d, J=3.0 Hz, 1H), 7.34-7.30 (m, 1H), 7.21 (dd, J=9.3, 3.0 Hz, 1H), 6.80 (d, J=9.3 Hz, 1H), 4.70 (s, 2H), 4.17 (q, J=7.1 Hz, 2H), 3.12 (s, 3H), 1.23 (t, J=7.1 Hz, 3H); ES-MS [M+1]+: 432.3.

Provenance & Evidence