反应详情

A solution of 2-(4-(5-nitro-1H-indol-3-yl)-5,6-dihydropyridin-1(2H)-yl)ethanol (0.225 g, 0.783 mmol) in dry methanol (5 mL) was treated with hydrazine hydrate (0.244 mL, 7.83 mmol), followed by Raney-nickel (0.1 g, 0.783 mmol) at room temperature. The resulting mixture was placed in a pre-heated oil bath and refluxed for 5 minutes (TLC basis, 2 M NH3 in MeOH:CH2Cl2, 1:9). The reaction was brought to room temperature, filtered through a Celite bed, and washed with methanol (3×10 mL). The combined methanol layer was evaporated and crude was purified by column chromatography (2 M NH3 in MeOH:CH2Cl2, 1:9) to obtain 2-(4-(5-amino-1H-indol-3-yl)-5,6-dihydropyridin-1(2H)-yl)ethanol (0.175 g, 87%) as a solid. 1H NMR (DMSO-d6) δ 10.59 (s, 1H), 7.15 (d, 1H, J=2.4 Hz), 7.05 (d, 1H, J=8.4 Hz), 6.99 (s, 1H), 6.48 (dd, 1H, J=1.8, 8.4 Hz), 5.96 (s, 1H), 4.48 (brs, 2H), 4.40 (t, 1H, J=5.4 Hz), 3.55 (q, 2H), 3.16-3.10 (m, 2H), 2.65 (t, 2H, J=5.7 Hz), 2.50-2.45 (m, 4H); ESI-MS (m/z, %): 258 (MH+, 30), 185 (100).

1. customThe resulting mixture was placed in a pre-heated oil bath
2. customwas brought to room temperature
3. filtrationfiltered through a Celite bed
4. washwashed with methanol (3×10 mL)
5. customThe combined methanol layer was evaporated
6. customcrude was purified by column chromatography (2 M NH3 in MeOH:CH2Cl2, 1:9)