[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[C:12]([Cl:29])[C:13]([CH2:17][N:18]3C(=O)C4C(=CC=CC=4)C3=O)=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.NN>CCO.O>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[C:12]([Cl:29])[C:13]([CH2:17][NH2:18])=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]To a stirred suspension of 318 (10.75 g, 0.026 mol) in EtOH (200 mL) was added hydrazine hydrate (2.52 mL, 0.052 mol), and the resulting reaction mixture was heated at 100° C. for 1 h. The cooled reaction mixture was diluted with water and thrice extracted with DCM. The combined organic layers were washed with water and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The solid was suspended in hexane (100 mL) and ethyl acetate (5 mL) and filtered. The filtrate was concentrated under reduced pressure to afford 5.34 g (73%) of tert-butyl-5-(aminomethyl)-4-chloro-1H-indol-1-carboxylate (320) as a white solid: 1H NMR (400 MHz, DMSO-d6) δ 7.97 (d, J=8.5 Hz, 1H), 7.73 (s, 1H), 7.50 (d, J=8.5 Hz, 1H), 6.71 (d, J=3.7 Hz, 1H), 2.09 (s, 2H), 1.63 (s, 9H); 2H not seen; MS (ESI) m/z=281.5 [M+1]+.
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