[CH3:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=2)[CH2:4][C:3]1=O.[C:17]1(C)C=CC=CC=1.[NH2:24][NH2:25]>CO>[CH3:1][C@@H:2]1[C:7]2[C:6](=[CH:17][NH:24][N:25]=2)[C@@H:5]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1(+/−)-(trans)-4-(4-Methyl-3-oxo-cyclohexyl)benzonitrile (0.55 g, 2.58 mmol) is added to toluene (10.0 mL) and tert-butoxybis(dimtheylamino)methane (0.67 mL, 3.22 mmols) and stirred at 120° C. for 16 hours. The mixture is cooled to room temperature and concentrated in vacuo. The residue is added to MeOH (10.0 mL) and hydrazine (0.07 mL, 2.32 mmol) and stirred at 80° C. for 1.0 hour. The mixture is cooled to room temperature and concentrated in vacuo. The residue is purified by silica gel chromatography (35%-55% EtOAc/hexanes) to give (+/−)-(trans)-4-[7-methyl-4,5,6,7-tetrahydro-2H-indazol-4-yl]benzonitrile (0.18 g, 29%).
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