Diisopropylethylamine → 4'-Fluoro-2'-methyl-biphenyl-3-carboxylic acid [4-(2-methylsulfanylpyrimidin-4-yloxy)-naphthalen-1-yl]-amide

Participants

Reaction Steps

4-(2-Methylsulfanylpyrimidin-4-yloxy)-naphthalen-1-ylamine (320 mg, 1 mmol), 3-(4-fluoro-2-methylphenyl)benzoic acid (230 mg, 1.0 mmol), HBTU (569 mg, 1.5 mmol) and diisopropylethylamine (0.53 ml, 3.0 mmol) are stirred at room temperature in anhydrous dimethylformamide (5 ml) for 1 day. The mixture is then poured into ethyl acetate (100 ml) and washed with water (100 ml). The organic layer is then dried over anhydrous sodium sulfate and evaporated to dryness. The residue is purified by column chromatography on silica gel eluted with 20-30-40% ethyl acetate in hexanes to give product as a pink solid recrystallized from ethyl acetate/hexanes to give 4′-fluoro-2′-methyl-biphenyl-3-carboxylic acid [4-(2-methylsulfanylpyrimidin-4-yloxy)-naphthalen-1-yl]-amide as pink crystals (67 mg). 1H NMR 400 MHz (CDCl3) 8.30 (d, 1H, J=6 Hz), 8.14 (s, 1H), 8.0 (d, 1H, J=8 Hz), 7.86-7.92 (m, 4H), 7.44-7.56 (m, 4H), 7.28 (d, 1H, J=8.4), 7.18 (m, 1H), 6.9-6.97 (m, 2H), 6.46 (d, 1H, J=5.6 Hz), 2.23 (d, 6H).

Provenance & Evidence