[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]3[CH2:11][CH2:12][N:13]([CH3:15])[CH2:14][C:5]=3[C:4]=2[CH:3]=1.[OH-].[K+].Br[CH2:19][C:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:21]>CN1C(=O)CCC1>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH2:19][C:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:21])[C:6]3[CH2:11][CH2:12][N:13]([CH3:15])[CH2:14][C:5]=3[C:4]=2[CH:3]=18-Chloro-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (220 mg, 10 mmol) was dissolved in NMP (2 mL). KOH (560 mg, 0.010 mol) was then added, followed by addition of 2-bromoacetophenone (199 mg, 0.001 mol). The reaction was kept overnight at RT and was monitored by TLC & LC/MS. The reaction was quenched by adding water, and extracted using EtOAc, which was then washed with water (2-3×). The organic layer was dried over sodium sulfate and then concentrated to yield 60 mg of dark brown crude oil that was purified by column chromatography using 100-200 mesh silica gel with 4% MeOH:DCM as eluent. 1HNMR (CDCl3, TFA salt) d (ppm): 8.0 (m, 2H), 7.70 (m, 1H), 7.60 (m, 2H), 7.40 (d, 1H), 7.20 (m, 1H), 7.05 (m, 1H), 5.60 (m, 1H), 5.38 (m, 1H), 4.80 (m, 1H), 4.20 (m, 1H), 3.90 (m, 1H), 3.40 (m, 2H), 3.05 (s, 3H), 1.90 (m, 1H).
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