Benzoyl Peroxide → Ethyl 4-bromo-7-hydroxy-3-phenylisoxazolo[4,5-c]pyridine-6-carboxylate

반응식

[OH:1][C:2]1[C:3]2[O:15][N:14]=[C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:4]=2[CH:5]=[N:6][C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9].C1C(=O)N([Br:29])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:29][C:5]1[C:4]2[C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:14][O:15][C:3]=2[C:2]([OH:1])=[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:6]=1

참가 물질

실험 절차

Ethyl 7-hydroxy-3-phenylisoxazolo[4,5-c]pyridine-6-carboxylate (1.0 g, 3.52 mmol), NBS (0.94 g, 5.28 mmol), and benzoyl peroxide (85 mg, 0.352 mmol) were added to 30 mL of carbon tetrachloride and refluxed for 16 h. Silica gel (10 g) was added and the solvent was evaporated. The crude was purified by flash chromatography (0-40% EtOAc/hexanes) to give 780 mg of the title compound. MS: (+) m/z 363.26, 365.17 (M+1, 79Br/81Br).