Cl.Cl[CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1.[OH-].[K+].[Cl:13][C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[NH:19][C:18]([CH3:23])=[CH:17]2.ClCCN1CCOCC1>CS(C)=O>[Cl:13][C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[N:19]([CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1)[C:18]([CH3:23])=[CH:17]2To a solution of 2-chloroethylmorpholine HCl (100 mg, 0.60 mmol) in 0.3 mL DMSO was added pulverized KOH (102 mg, 1.81 mmol), then after 10 min, a solution of 5-chloro-2-methylindole (134 mg, 0.72 mmol) in 0.2 mL DMSO was added and the reaction stirred at room temperature overnight. Additional 2-chloroethylmorpholine (22 mg, 0.12 mmol) and KOH (17 mg, 0.3 mmol) added and stirred overnight. The reaction mixture was partitioned between H2O and toluene, and the organic extract washed two times with H2O, dried over MgSO4, filtered, and concentrated in vacuo. The crude product was purified via silica gel chromatography using a gradient from 0 to 5% MeOH in CH2Cl2 to give a final yield of 154 mg (0.55 mmol). 1H NMR (500 MHz, CDCl3, δ): 2.47 (s, 3H), 2.48-2.57 (m, 4H), 2.63 (t, J=7.2 Hz, 2H), 3.73 (t, J=4.4 Hz, 4H), 4.16 (t, J=7.2 Hz, 2H), 6.20 (s, 1H), 7.11 (dd, J=8.6 Hz, 1.7 Hz, 1H), 7.19 (d, J=8.6 Hz, 1H), 7.50 (d, J=1.5 Hz, 1H). 13C NMR (500 MHz, CDCl3, δ): 12.88, 41.23, 54.13, 57.86, 66.95, 99.88, 109.78, 119.15, 120.64, 124.97, 129.18, 134.99, 138.03. MS m/z 279.3 [M+H]+.
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