[Cl:1][C:2]1[CH:3]=[C:4]([C:18]#[N:19])[C:5]2[C:6]([CH3:17])=[N:7][N:8]([CH:11]3[CH2:16][CH2:15][CH2:14][CH2:13][O:12]3)[C:9]=2[CH:10]=1>[Ni].N.CO>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH3:17])=[N:7][N:8]2[CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)=[C:4]([CH2:18][NH2:19])[CH:3]=1A mixture of 6-chloro-3-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-4-carbonitrile (150 mg, 0.545 mmol) and Raney nickel (20 mg) in NH3/MeOH (7 N, 10 mL) was stirred under hydrogen at RT overnight. The reaction mixture was filtered through Celite® and the filtrate concentrated to afford (6-chloro-3-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl)methanamine (123) as an oil (130 mg, 72.3%). MS (ESI): m/z=280 [M+1]+.
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