ClC1N=C(C2NC3C(C=2)=CC=CC=3)C(O)=CC=1.ClCI.C([O-])([O-])=O.[K+].[K+].[Cl:27][C:28]1[CH:29]=[CH:30][C:31]2[O:43][CH2:42][N:34]3[C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][C:40]=4[CH:41]=[C:33]3[C:32]=2[N:44]=1>CN(C=O)C.O>[Cl:27][C:28]1[CH:29]=[CH:30][C:31]2[O:43][CH2:42][C:41]3[C:40]4[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=4)[NH:34][C:33]=3[C:32]=2[N:44]=1
A solution of 6-chloro-2-(1H-indol-2-yl)pyridin-3-ol (500 mg, 3.05 mmol) in DMF (50 mL) was added dropwise to a mixture of chloroiodomethane (5.37 g, 30.5 mmol) and K2CO3 (1.26 g, 9.15 mmol) in DMF (50 mL) at 100° C. After addition, the mixture was diluted with water (100 mL) and extracted with EtOAc (50 mL*3). The organic layer was washed with brine (50 mL*3), dried over Na2SO4 and concentrated in vacuo. The resulting residue was purified using chromatography (petroleum ether:EtOAc=30:1) to provide the mixture of 2-chloro-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indole and 2-chloro-6,11-dihydropyrido[2′,3′:5,6]pyrano[4,3-b]indole (ratio=3:1, 80 mg, yield: 15.3%), which was further purified with prep-HPLC to provide both of the isomers. MS (M+H)+: 257/259.
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