Carbon Tetrachloride → Ethyl 4-(bromomethyl)-3-(4-methoxyphenyl)-7-(pivaloyloxy)isoxazolo[4,5-c]pyridine-6-carboxylate

Participants

Reaction Steps

Ethyl 3-(4-methoxyphenyl)-4-methyl-7-(pivaloyloxy)isoxazolo[4,5-c]pyridine-6-carboxylate (58 mg, 0.14 mmol), NBS (28 mg, 0.15 mmol) and benzoyl peroxide (3.4 mg, 0.014 mmol) were added to 3 mL of carbon tetrachloride. The mixture was refluxed for 16 h. After the mixture was cooled to room temperature, another 1 equiv of NBS and 0.1 equiv of benzoyl peroxide were added, and the reaction mixture was refluxed for an additional 16 h. After the mixture was cooled, 20 mL of CH2Cl2 and 1 g of silica gel were added, and the solvent was removed in vacuo. The crude was purified by flash chromatography (0-30% EtOAc/hexanes) to give 34 mg of the title compound. MS: (+) m/z 491.28, 493.25 (M+1, 79Br/81Br).

Provenance & Evidence