Potassium Carbonate → HCID 76280796, compound

Participants

Reaction Steps

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 (5 mg, 0.02 mmol), KF (8 mg, 0.14 mmol), and 2-bromobenzyl bromide (20 mg, 0.10 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 and purified by chromatography (35% EtOAc/hexanes) to give 3-[4-(2-bromo-benzyloxy)-phenyl]-isoxazole-5-carboxylic acid amide (7.5 mg, 16%) as a white powder. LRMS (ESI+): m/z [M+H]+ 376.1. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.35 (s, 1H), 7.98 (s, 1H), 7.85 (d, J=8.8 Hz, 2H), 7.64-7.72 (m, 1H), 7.59 (d, J=7.7 Hz, 1H), 7.53 (s, 1H), 7.39-7.48 (m, 1H), 7.26-7.36 (m, 1H), 7.16 (d, J=8.8 Hz, 2H), 5.19 (s, 2H).

Provenance & Evidence