C(C1[C:5]([C:11]2[NH:12][C:13]3[C:18]([CH:19]=2)=[C:17]([F:20])[CH:16]=[CH:15][CH:14]=3)=[N:6][C:7]([Cl:10])=[CH:8][CH:9]=1)C=C.C[N+]1([O-])CC[O:25]CC1.[O-]S([O-])(=S)=O.[Na+].[Na+].[CH2:36]1[CH2:40][O:39][CH2:38][CH2:37]1>O.O=[Os](=O)(=O)=O>[Cl:10][C:7]1[N:6]=[C:5]([C:11]2[NH:12][C:13]3[C:18]([CH:19]=2)=[C:17]([F:20])[CH:16]=[CH:15][CH:14]=3)[C:38]([CH2:37][CH:36]([OH:25])[CH2:40][OH:39])=[CH:9][CH:8]=1A mixture of 2-(3-allyl-6-chloropyridin-2-yl)-4-fluoro-1H-indole (100 mg, 0.35 mmol) and NMO (124 mg, 1.05 mmol) in THF (5 mL) and H2O (2.5 mL) was stirred at 0° C. Then OsO4 (20 mg) was added, and the mixture was stirred at RT overnight. After cooling to 0° C., a.q. Na2S2O3 was added and extracted with CH2Cl2. Then the organic layer was washed with water, brine, dried over Na2SO4 and concentrated on a rotary evaporator. The residue was purified by column chromatography (PE:EA=2:1˜1:1) to give the product of 3-(6-chloro-2-(4-fluoro-1H-indol-2-yl)pyridin-3-yl)propane-1,2-diol (100 mg, yield: 89%). 1H-NMR (CDCl3, 400 MHz) δ 9.88 (s, 1H), 7.65 (d, J=8.4 Hz, 1H), 7.12˜7.18 (m, 3H), 7.02 (s, 1H), 6.76 (t, J=8.0 Hz, 1H), 4.12˜4.16 (m, 1H), 3.81˜3.85 (m, 1H), 3.64˜3.67 (m, 1H), 3.07˜3.15 (m, 2H). MS (M+H)+: 321/323.
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