OO.[CH3:3][C:4]1[C:12]([O:13][C:14]2[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][N:15]=2)=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][CH2:7][C:8]2=[O:22].C([O-])([O-])=[O:24].[K+].[K+].CS(C)=O>O>[CH3:3][C:4]1[C:12]([O:13][C:14]2[CH:21]=[CH:20][C:17]([C:18]([NH2:19])=[O:24])=[CH:16][N:15]=2)=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][CH2:7][C:8]2=[O:22]Add 30% aqueous H2O2 (3.6 ml) to a suspension of 6-(4-Methyl-1-oxo-indan-5-yloxy)-nicotinonitrile (1.22 mg, 4.61 mmol), K2CO3 (319 mg, 2.31 mmol) and DMSO (20 ml) stirring under nitrogen at ambient temperature. After 2.5 hours, dilute the reaction mixture with water (100 ml) and extract with EtOAc (2×). Wash the extract with water and brine, dry (MgSO4) and concentrate on rotary evaporator to yield 1.07 g of the title compound as a yellow solid. Mass spectrum (ion spray): m/z=283 (M+1); 1HNMR (DMSO-d6): 8.55 (s, 1H), 8.27 (d, 1H), 8.01 (s, 1H), 7.51 (d, 1H), 7.47 (s, 1H), 7.17 (d, 1H), 7.12 (d, 1H), 3.03 (t, 2H), 2.66 (t, 2H), 2.07 (s, 3H).
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