[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.CS(C)=O.[OH-].[K+]>[N+](CCCC)(CCCC)(CCCC)CCCC.[Cl-].O>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[CH2:18][CH2:19][N:9]3[C:10]4[CH:11]=[CH:12][CH:13]=[C:14]([F:17])[C:15]=4[CH:16]=[C:8]3[C:6]=2[CH:7]=1A solution of 2-(2-chloro-5-vinylpyridin-4-yl)-4-fluoro-1H-indole (50 mg, 0.18 mmol), Bu4NCl (0.07 mL of 50% a.q. solution), DMSO (0.25 mL) and KOH (0.6 mL of 60% a.q. solution) was stirred at 100° C. for 3 hours. Then the mixture was diluted with H2O, extracted with EtOAc, then the combined organic phase was washed with brine, dried over Na2SO4 and concentrated in vacuo to give the crude product. It was purified by column (PE:EA=3:1) to obtain the product of 2-chloro-11-fluoro-5,6-dihydroindolo[2,1-a][2,6]naphthyridine (11 mg, yield: 20%). 1H-NMR (CDCl3, 400 MHz) δ 8.30 (s, 1H), 7.62 (s, 1H), 7.18˜7.21 (m, 2H), 7.12 (s, 1H), 6.81 (t, J=8.4 Hz, 1H), 4.29 (t, J=6.0 Hz, 2H), 3.20 (t, J=6.0 Hz, 2H). MS (M+H)+: 273/275.
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