[C:1]([O-])([O-])=O.[Cs+].[Cs+].IC.[Br:9][C:10]1[CH:22]=[C:21]2[C:13]([C:14]3[CH2:15][CH2:16][CH2:17][C:18](=[O:23])[C:19]=3[NH:20]2)=[CH:12][CH:11]=1>CN(C=O)C.O>[Br:9][C:10]1[CH:22]=[C:21]2[C:13]([C:14]3[CH2:15][CH2:16][CH2:17][C:18](=[O:23])[C:19]=3[N:20]2[CH3:1])=[CH:12][CH:11]=1Cs2CO3 (2.5 g, 7.5 mmol) and iodomethane (0.47 mL, 7.5 mmol) were added to a solution of 7-bromo-2,3,4,9-tetrahydro-1H-carbazol-1-one (1.7 g, 6.3 mmol) in DMF (21 mL), and the resulting mixture was stirred for 4 h at ambient temperature. The reaction was diluted with H2O (25 mL), and the resulting solution was stirred for 15 minutes. The resulting precipitate was collected by filtration, washed with H2O (200 mL) and dried to yield the title compound (1.5 g, 87%) as an off-white powder: 1H NMR (500 MHz, DMSO-d6) δ 7.83 (d, J=1.5 Hz, 1H), 7.67 (d, J=8.5 Hz, 1H), 7.25 (dd, J=8.5, 1.5 Hz, 1H), 3.98 (s, 3H), 2.96 (t, J=6.0 Hz, 2H), 2.57 (t, J=6.0 Hz, 2H), 2.13-2.10 (m, 2H).
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