N,N-Dimethylglycine → 1-(4-Fluorophenyl)-6-((6-methylpyridin-3-yl)oxy)-4-oxo-1,4-dihydroquinoline-3-carboxamide

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Reaction Conditions

Reaction Steps

Compound E (15 mg, 0.042 mmol, 1.0 eq), 5-hydroxy-2-methylpyridine (9.1 mg, 0.083 mmol, 2.0 eq), cesium carbonate (27 mg, 0.083 mmol, 2.0 eq), copper(I) iodide (0.79 mg, 0.0042 mmol, 0.10 eq) and N,N-dimethylglycine (1.3 mg, 0.013 mmol, 0.30 eq) were dissolved in DMF in a microwave vial and heated in a microwave reactor at 150° C. for 15 minutes. The reaction was filtered over Celite® and washed with 5% methanol in DCM. The organics were concentrated and purified using reverse phase chromatography to afford 9.1 mg (56%) of title compound as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 9.12 (d, J=4.3 Hz, 1H), 8.54 (s, 1H), 8.33 (d, J=2.8 Hz, 1H), 7.77-7.73 (m, 2H), 7.68 (d, J=3.0 Hz, 1H), 7.59 (d, J=4.3 Hz, 1H), 7.56-7.47 (m, 4H), 7.34 (d, J=8.5 Hz, 1H), 7.12 (d, J=9.2 Hz, 1H), 2.49 (s, 3H); ES-MS [M+1]+: 390.4.

Provenance & Evidence