[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][C:3]=1[C:11]#[N:12]>CO.N.[Ni]>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][C:3]=1[CH2:11][NH2:12]To a solution of 242 (43 mg, 0.24 mmol) in MeOH (10 mL) and 7M NH3 in MeOH (5 mL) was added Raney nickel and the reaction mixture was stirred vigorously under hydrogen (1 atm.) at RT for 3 h. The reaction mixture was filtered through a pad of Celite® and concentrated under reduced pressure to afford (6-chloro-1H-indol-5-yl)methanamine (244) as pale oil: MS (ESI)=164.1 [M−NH2]+.
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