3-Chlorophenol → 3-[4-(3-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; 40 mg, 0.142 mmol) in CH3CN (2 mL) were added 3-chlorophenol (28 mg, 0.22 mmol) and K2CO3 (40 mg, 0.29 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-(3-chloro-phenoxymethyl)-phenyl]-isoxazole-5-carboxylic acid amide (33 mg, 71%) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.38 (br. s., 1H), 8.01 (br. s., 1H), 7.92 (d, J=8.1 Hz, 2H), 7.55-7.66 (m, 3H), 7.23-7.36 (m, 1H), 7.09-7.15 (m, 1H), 6.95-7.05 (m, 2H), 5.21 (s, 2H).

Provenance & Evidence