Sodium Carbonate → Ethyl 4-(3-methyl-5-nitro-4-oxo-1,4-dihydroquinolin-8-yl)cyclohex-3-ene-1-carboxylate

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A mixture of 8-bromo-3-methyl-5-nitroquinolin-4(1H)-one (Compound 304E, 700 mg, 2.47 mmol), ethyl 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)cyclohex-3-enecarboxylate (1.8 g, 6.43 mmol, commercially available or can be prepared according to WO2008/099221), Pd(PPh3)4 (20 mg), and Na2CO3 (1 g, 9.43 mmol) in 1,4-dioxane/H2O (150 mL, 4:1) was evacuated and purged with N2. The reaction mixture was stirred at 100° C. for 18 h under N2. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The material was purified by flash column chromatography to afford the desired compound (600 mg, yield: 67%). 1H NMR (DMSO-d6, 400 MHz): δ=1.22 (t, J=7.2 Hz, 3 H), 1.85 (m, 1 H), 1.96 (s, 3 H), 2.08 (m, 1 H), 2.26 (m, 1 H), 2.38-2.49 (m, 3 H), 2.78 (m, 1 H), 4.12 (q, J=7.2 Hz, 2 H), 5.84 (s, 1 H), 7.46 (d, J=8.0 Hz, 1 H), 7.58 (d, J=8.0 Hz, 1 H), 7.83 (d, J=6.0 Hz, 1 H), 10.94 (d, J=6.0 Hz, 1 H).

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