[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]([OH:11])CO)=[C:4]([C:12]2[NH:13][C:14]3[C:19]([CH:20]=2)=[C:18]([F:21])[CH:17]=[CH:16][CH:15]=3)[CH:3]=1.[O-]S([O-])=O.[Na+].[Na+].O>C1COCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[NH:13][C:14]3[C:19]([CH:20]=2)=[C:18]([F:21])[CH:17]=[CH:16][CH:15]=3)[C:5]([CH:8]=[O:11])=[CH:6][N:7]=1To a solution of 1-(6-chloro-4-(4-fluoro-1H-indol-2-yl)pyridin-3-yl)ethane-1,2-diol (1.9 g, 6.21 mmol) in THF—H2O (26 mL-13 mL), NaIO4 (1.94 g, 9.31 mmol) was added, the reaction mixture was stirred at room temperature for 2 hours. Then Na2SO3 and water were added and the mixture was stirred at room temperature for 30 min. The mixture was extracted with EA. The organic layer was washed with brine, dried over Na2SO4 and concentrated. The residue was purified by column chromatography (DCM:MeOH=20:1) to afford the desired product of 6-chloro-4-(4-fluoro-1H-indol-2-yl)nicotinaldehyde (1.4 g, yield: 82.4%). 1H-NMR (Methanol-d4, 400 MHz) δ 8.48 (s, 1H), 7.79 (s, 1H), 7.40 (d, J=8.4 Hz, 1H), 7.17˜7.25 (m, 1H), 6.95 (s, 1H), 6.79 (dd, J=8.0, 10.0 Hz, 1H), 6.70 (s, 1H). MS (M+H)+: 275/277.
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