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

反応式

[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

参加物

実験手順

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).