4-Fluoroaniline → Ethyl 6-bromo-1-(4-fluorophenyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

Compound C (2.87 g, 9.93 mmol, 1.00 eq) and N,N-dimethylformamide dimethyl acetal (1.87 mL, 14.9 mmol, 1.50 eq) were dissolved in DMF (33 mL) in a microwave vial and heated in a microwave reactor at 120° C. for 15 minutes. To this mixture was then added 4-fluoroaniline (1.41 mL, 14.9 mmol, 1.50 eq) and the reaction was heated in a microwave reactor at 150° C. for 20 minutes. The reaction mixture was diluted with ethyl acetate and washed with water (2×). The aqueous layers were back-extracted with ethyl acetate and the combined organics were dried (MgSO4), filtered and concentrated in vacuo. Purification by flash chromatography on silica gel using 0-45% hexanes/ethyl acetate afforded 3.79 g (98%) of the title compound as yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 8.47 (s, 1H), 8.31 (d, J=2.4 Hz, 1H), 7.81 (dd, J=9.1, 2.4 Hz, 1H), 7.77-7.73 (m, 2H), 7.54-7.50 (m, 2H), 6.92 (d, J=9.0 Hz, 1H), 4.20 (q, J=7.1 Hz, 2H), 1.25 (t, J=7.1 Hz, 3H); ES-MS [M+1]+: 390.2.

Provenance & Evidence