O-Cresol → 3-(4-o-Tolyloxymethyl-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 o-cresol (20 mg, 0.185 mmol) and K2CO3 (30 mg, 0.22 mmol). The mixture was heated at 90° C. for 16 h and then evaporated to dryness. The residue was purified by chromatography (66-75% EtOAc/hexanes) to give 3-(4-o-tolyloxymethyl-phenyl)-isoxazole-5-carboxylic acid amide (21 mg, 64%) as a white powder. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.38 (br. s., 1H), 8.00 (br. s., 1H), 7.92 (d, J=8.1 Hz, 2H), 7.53-7.67 (m, 3H), 7.05-7.20 (m, 2H), 6.99 (d, J=7.7 Hz, 1H), 6.74-6.90 (m, 1H), 5.19 (s, 2H), 2.21 (s, 3H).

Provenance & Evidence