Hydrazine → HCID 69435001, compound

A large excess of Raney® nickel was added in portions to a stirred solution of ethyl 1-(4-nitrobenzyl)-1H-indole-2-carboxylate (0.65 g, 2 mmol), hydrazine (0.5 mL, 16 mmol) in 25 mL of ethanol. After stirring at room temperature for 2 hours the catalyst was then removed by filtering through a short pad of Celite®521. The filtrate was concentrated to give ethyl 1-(4-aminobenzyl)-1H-indole-2-carboxylate (MS (ESI) m/z 294.2 (MH+) as a gummy solid. The gummy solid was then dissolved in 15 mL of methylene chloride. To the solution was added diisopropylethylamine (0.5 mL, 2.9 mmol) and biphenyl 4-sulfonyl chloride (0.5 g, 1.0 mmol). After being stirred at room temperature overnight the reaction was concentracted and the residue was re-dissolved in 15 mL of 2:1:1 THF/MeOH/water. Lithium hydroxide monohydrate (0.2 g, 4.8 mmol) was added and the mixture was stirred at room temperature overnight. Most of the organic solvents was removed and the reaction mixture was made acidic (pH 6) with glacial acetic acid, and the solid was collected and purified by semi-preparative HPLC. The product was collected based on UV absorption and concentrated to give the title compound as a brown solid (0.11 g, 22%): 1H NMR (DMSO-d6) δ 5.75 (s, 2H), 6.93 (d, J=8.9 Hz, 2H), 7.01 (d, J=8.9 Hz, 2H), 7.09 (t, J=8.0 Hz, 1H), 7.43 (t, J=8.0 Hz, 1H), 7.49 (s, 1H), 7.40-7.55 (m, 4H); 7.65-7.80 (m, 3H), 7.75-7.82 (m, 4H), 10.30 (s, 1H), 12.93 (s, 1H); HRMS calcd for C28H23N2O4S: 483.1367; found (ESI+): 483.1374; Anal. calcd for C28H22N2O4S .0.2H2O: C, 69.18; H, 4.64; N, 5.76. Found: C, 69.21; H, 4.60; N, 5.78.