3-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-isoxazole-5-carboxylic acid amide (which may be prepared as described in Preparation of Intermediate 13; 40 mg, 0.126 mmol) was dissolved in DMF (1.5 mL). K2CO3 (19 mg, 0.14 mmol), 18-crown-6 (6 mg, 0.02 mmol), KF (8 mg, 0.14 mmol), and 3-chlorobenzyl chloride (20 μL, 0.129 mmol) were added. The reaction mixture was stirred at room temperature for 10 min and then at 40° C. for 12 h. H2O (2.5 mL) was added and the mixture was extracted with EtOAc. The organic layer was evaporated to give 3-[4-(3-chloro-benzyloxy)-phenyl]-isoxazole-5-carboxylic acid amide (31.8 mg, 77%) as an off-white powder. HRMS Calcd. for C17H13ClN2O3 (M+), 328.0615. Found: 328.0612.
