[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[NH:9][C:10]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:5]([OH:17])=[CH:4][CH:3]=1.[C:18]([O-])([O-])=O.[K+].[K+].ClCI>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:17][CH2:18][N:9]3[C:10]4[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=4[CH:16]=[C:8]3[C:6]=2[N:7]=1To a solution of 6-chloro-2-(1H-indol-2-yl)pyridin-3-ol (480 mg, 2.0 mmol) and K2CO3 (1.38 g, 10.0 mmol) in DMF (50 mL) stirring at 100° C., chloroiodomethane (386 mg, 2.2 mmol) in DMF (10 mL) was added dropwise. After addition, the mixture was allowed to stir for another 0.5 hours. The mixture was then diluted with water (100 mL) and extracted with EtOAc (100 mL*3). The organic layer was washed with brine (100 mL*3), dried over Na2SO4 and concentrated in vacuo. The resulting residue was purified using prep-TLC (petroleum ether:EtOAc=3:1) to provide the product 2-chloro-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indole (260 mg, yield: 50.7%). 1H-NMR (CDCl3, 400 MHz) δ 7.63 (d, J=8.0 Hz, 1H), 7.22˜7.27 (m, 3H), 7.19 (d, J=2.4 Hz, 1H), 7.08˜7.12 (m, 2H), 5.86 (s, 2H). MS (M+H)+: 257/259.
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