4-Methoxyphenol → 3-[4-(4-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 4-methoxyphenol (24 mg, 0.22 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-(4-methoxy-phenoxymethyl)-phenyl]-isoxazole-5-carboxylic acid amide (12 mg, 35%) as a white powder. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.38 (br. s., 1H), 8.00 (br. s., 1H), 7.90 (d, J=8.4 Hz, 2H), 7.52-7.64 (m, 3H), 6.90-7.00 (m, 1H), 6.81-6.89 (m, 1H), 5.11 (s, 1H), 3.26-3.34 (m, 3H).

Provenance & Evidence