[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:13]2=[N:14][CH:15]=[CH:16][C:17]([C:18]3[CH:19]=[N:20][CH:21]=[N:22][CH:23]=3)=[C:12]2[O:11][N:10]=1.C(OO)(=[O:26])C.S(=O)(=O)(O)O.[OH-].[Na+]>CC(C)=O>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:13]2=[N:14][CH:15]=[CH:16][C:17]([C:18]3[C:23]([OH:26])=[N:22][CH:21]=[N:20][CH:19]=3)=[C:12]2[O:11][N:10]=1To a vial charged with 3-(2-chloro-4-fluorophenyl)-7-(pyrimidin-5-yl) isoxazolo[4,5-b]pyridine (4.8 mg, 0.015 mmol) in acetone (Volume: 100 μl) were added peroxyacetic acid (6.18 μl, 0.029 mmol) and sulfuric acid (1.632 μl, 0.029 mmol). The reaction mixture was refluxed for 75 min, and then allowed to cool to room temperature. The reaction mixture was neutralized with 4 M NaOH and extracted with CH2Cl2 (5×). The organic phases were combined, dried over Na2SO4, filtered, and concentrated to afford the title compound as a yellow residue (5.0 mg, 99%). ESI MS (M+H)+=343.0.
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