[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[Cl-].C[CH:13]=[N+:14]=[CH:15]C.O.[OH-].[Na+].[CH2:20](Cl)Cl>>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:13][N:14]([CH3:15])[CH3:20])=[CH:7][NH:8]2)=[CH:4][CH:3]=1To a solution of 6-bromoindole (7.18 g, 36.6 mmol) in CH2Cl2 (140 mL) was added N,N-dimethylmethylene ammonium chloride (5.48 g, 58.6 mmol, 1.60 eq.) in one portion and the resultant mixture was stirred at rt for 2 h under N2. Water (150 mL) and 1M NaOH (62 mL, 62 mmol) were added, and the reaction mixture was extracted with EtOAc (300 mL). The organic layer was washed with aqueous saturated NaCl and dried (MgSO4). The solvent was removed in vacuo to give 9.29 g (100%) of the title compound.
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