4-Bromo-1-naphthylamine → N-(4-bromo-naphthalen-1-yl)-3-fluoro-5-morpholin-4-yl-benzamide

Participants

Reaction Steps

3-Fluoro-5-morpholin-4-yl-benzoic acid (4.45 g, 19.8 mmol) and HBTU (8.19 g, 21.6 mmol) are stirred at room temperature in dry DMF (40 ml) for 1 hour. 4-Bromo-naphthalen-1-ylamine (4.0 g, 18.0 mmol) and diisopropylethylamine (4.8 ml, 27 mmol) are then added and the mixture is stirred at room temperature for 16 hours. The mixture is poured into ethyl acetate (300 ml) and washed with water (250 ml). The organic layer is dried over anhydrous sodium sulfate and evaporated to dryness. The residue is crystallized from ethyl acetate and hexanes to give N-(4-bromo-naphthalen-1-yl)-3-fluoro-5-morpholin-4-yl-benzamide as a pink powder (1.688 g). Mp: 195-6° C. 1H NMR 300 MHz (DMSO-d6) δ 10.5 (s, 1H), 8.19 (d, 1H, J=6 Hz), 8.04 (d, 1H, J=8.4 Hz), 7.94 (d, 1H, J=8.4 Hz), 7.71 (m, 2H), 7.53 (d, 1H, J=8.1Hz), 7.47 (s, 1H), 7.25 (d, 1H, J=8.4 Hz), 7.05 (d, 1H, J=12.3 Hz), 3.76 (s, 4H), 3.26 (s, 4H). MS: 429 (M+1).

Provenance & Evidence