[CH2:1]([C:3]1([C:13]2[C:21]3[C:16](=[C:17]([N+:22]([O-:24])=[O:23])[CH:18]=[CH:19][CH:20]=3)[NH:15][CH:14]=2)[C:11]2[C:6](=[CH:7][C:8]([F:12])=[CH:9][CH:10]=2)[CH2:5][CH2:4]1)[CH3:2].[CH3:25][O-].[Na+].IC>CN(C)C=O.CCOCC>[CH2:1]([C:3]1([C:13]2[C:21]3[C:16](=[C:17]([N+:22]([O-:24])=[O:23])[CH:18]=[CH:19][CH:20]=3)[N:15]([CH3:25])[CH:14]=2)[C:11]2[C:6](=[CH:7][C:8]([F:12])=[CH:9][CH:10]=2)[CH2:5][CH2:4]1)[CH3:2]Combine 3-(1-ethyl-5-fluoro-indan-1-yl)-7-nitro-1H-indole (0.33 g, 1.02 mmol), sodium methoxide (110 mg, 2.04 mmol), and iodomethane (0.10 ml, 1.53 mmol) in dimethylformamide (5 ml) and stir at room temperature under nitrogen overnight. Dilute with ether, wash with water (2×), dry over sodium sulfate, filter, and concentrate to obtain the title compound as a yellow amorphous solid (0.33 g, 94%). LC-MS m/z 339.1 (M++1).
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