Ethyl Acetate → 4'-Fluoro-2'-methyl-biphenyl-3-carboxylic acid [4-(2-morpholin-4-yl-ethoxy)-naphthalen-1-yl]-amide

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Reaction Steps

3-Bromo-N-[4-(2-morpholin-4-yl-ethoxy)-naphthalen-1-yl]-benzamide (600 mg, 1.31 mmol), 4-fluoro-2-methylphenyl boronic acid (271 mg, 1.98 mmol), cesium carbonate (730 mg, 2.24 mmol) and tetrakis triphenylphosphine palladium(0) (25 mg) in dioxane (10 ml) are heated to 100° C. under a nitrogen atmosphere for 16 hours. The mixture is cooled to room temperature then poured into ethyl acetate (100 ml). The organic layer is washed with water (100 ml), dried over anhydrous sodium sulfate and evaporated to dryness. The residue is then purified by column chromatography on silica gel to give 4′-fluoro-2′-methyl-biphenyl-3-carboxylic acid [4-(2-morpholin-4-yl-ethoxy)-naphthalen-1-yl]-amide as pale purple needles (0.44 g). Mp: 95-7° C. 1H NMR 300 MHz (CDCl3) δ 8.35 (d, 1H, J=7.5 Hz), 7.85-8.1 (m, 5H), 7.75 (d, 1H, J=7.5 Hz), 7.5-7.63 (m, 4H), 7.2 (m, 1H), 6.9-7.05 (m, 2H), 6.85 (d, 1H, J=12 Hz), 4.3 (t, 2H), 3.75 (m, 4H), 2.98 (t, 2H), 2.6 (m, 4H), 2.3 (s, 3H).

Provenance & Evidence