3-Methoxyphenol → 3-[4-(3-Methoxy-phenoxymethyl)-phenyl]-isoxazole-5-carboxylic acid amide

Participants

Reaction Conditions

Reaction Steps

To a mixture of 3-(4-bromomethyl-phenyl)-isoxazole-5-carboxylic acid amide (which may be prepared as described in Preparation of Intermediate 14; 30 mg, 0.107 mmol) in CH3CN (2 mL) were added 3-methoxyphenol (21 μL, 0.19 mmol) and K2CO3 (30 mg, 0.22 mmol). The mixture was heated at 85° C. for 16 h and then evaporated to dryness. The residue was purified by chromatography (66-75% EtOAc/hexanes) to give 3-[4-(3-methoxy-phenoxymethyl)-phenyl]-isoxazole-5-carboxylic acid amide (20 mg, 58%) as a white powder. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.38 (br. s., 1H), 8.00 (br. s., 1H), 7.91 (d, J=8.1 Hz, 2H), 7.54-7.62 (m, 3H), 7.18 (t, J=7.9 Hz, 1H), 6.47-6.64 (m, 3H), 5.16 (s, 2H), 3.26-3.33 (m, 3H).

Provenance & Evidence