Hydrazine → 4-Bromo-7-methoxy-1H-indole
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[Br:1][C:2]1[C:7](/[CH:8]=[CH:9]/N2CCCC2)=[C:6]([N+:15]([O-])=O)[C:5]([O:18][CH3:19])=[CH:4][CH:3]=1.NN>C1COCC1.CO.[Ni]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:18][CH3:19])=[C:6]2[C:7]=1[CH:8]=[CH:9][NH:15]2[Br:1][C:2]1[C:7](/[CH:8]=[CH:9]/N2CCCC2)=[C:6]([N+:15]([O-])=O)[C:5]([O:18][CH3:19])=[CH:4][CH:3]=1.NN>C1COCC1.CO.[Ni]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:18][CH3:19])=[C:6]2[C:7]=1[CH:8]=[CH:9][NH:15]2To a solution of 1-[(E)-2-(6-bromo-3-methoxy-2-nitrophenyl)vinyl]pyrrolidine (1.3 g, 3.97 mmol) in THF (6 mL) and methanol (6 mL) was added Raney Ni (≈500 mg) followed by hydrazine (0.19 mL). (CAUTION: Exothermic reaction with vigorous gas evolution). Hydrazine (0.19 mL) was added again, two times, after 30 min and 1 h. The reaction was stirred at 45° C. for 2 h, filtered through a pad of celite. The filtrate was concentrated in vacuo and the residue purified by chromatography over silica gel eluting with EtOAc/hexane to afford pure 4-bromo-7-methoxy-1H-indole. 1H NMR (400 MHz, CDCl3) δ=3.94 (s, 3H), 6.52 (d, J=8.08 Hz, 1H), 6.56 (dd, J=3.16, 2.40 Hz, 1H), 7.17 (d, J=8.08 Hz, 1H), 7.22 (t, J=2.78 Hz, 1H) and 8.47 (br. s., 1H); MS (ES+): m/z 226.12 [MH+].
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