[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[NH:9][C:10]3[C:15]([CH:16]=2)=[C:14]([F:17])[CH:13]=[CH:12][CH:11]=3)[C:5]([CH:18]=[CH2:19])=[CH:4][N:3]=1.C[N+]1([O-])CC[O:24]CC1.[O-]S([O-])=O.[Na+].[Na+].[OH2:34]>C1COCC1.O.O=[Os](=O)(=O)=O>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([CH:18]([OH:24])[CH2:19][OH:34])=[C:6]([C:8]2[NH:9][C:10]3[C:15]([CH:16]=2)=[C:14]([F:17])[CH:13]=[CH:12][CH:11]=3)[CH:7]=1To a solution of 2-(2-chloro-5-vinylpyridin-4-yl)-4-fluoro-1H-indole (2 g, 7.35 mmol) in THF—H2O (26 mL-13 mL), NMO (2.15 g, 18.38 mmol) and OsO4 (56 mg, 0.22 mmol) were added. The reaction mixture was stirred at room temperature for 2 hours. Then Na2SO3 and water were added. The mixture was stirred at room temperature for 20 min and filtered. The filtrate 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=10:1) to give 1-(6-chloro-4-(4-fluoro-1H-indol-2-yl)pyridin-3-yl)ethane-1,2-diol (1.9 g, yield: 84.4%). 1H-NMR (Methanol-d4, 400 MHz) 8.61 (s, 1H), 7.63 (s, 1H), 7.24 (d, J=8.0 Hz, 1H), 7.08˜7.19 (m, 1H), 6.90 (s, 1H), 6.75 (dd, J=7.6, 10.0 Hz, 1H), 5.19 (t, J=6.0 Hz, 1H), 3.75˜3.82 (m, 1H), 3.67˜3.74 (m, 1H). MS (M+H)+: 307/309.
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