4-Chlorophenol → 3-[4-(4-Chloro-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-chlorophenol (21 mg, 0.16 mmol) and K2CO3 (30 mg, 0.22 mmol). The mixture was heated at 90° C. for 4 h and then evaporated to dryness. The residue was purified by chromatography (66-75% EtOAc/hexanes) to give 3-[4-(4-chloro-phenoxymethyl)-phenyl]-isoxazole-5-carboxylic acid amide (29 mg, 82%) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.39 (s, 1H), 8.01 (s, 1H), 7.91 (d, J=8.2 Hz, 2H), 7.50-7.65 (m, 3H), 7.26-7.38 (m, 2H), 6.97-7.11 (m, 2H), 5.17 (s, 2H).

Provenance & Evidence