反应详情

A solution of 3-(2-(pyrrolidin-1-yl)ethyl)-1H-indol-5-amine (0.59 g, 2.57 mmol) in dry ethanol (10 mL) was treated with methyl thiophene-2-carbimidothioate hydroiodide (1.467 g, 5.15 mmol) at room temperature and the resulting mixture was stirred overnight. The reaction was basified with saturated NaHCO3 solution (50 mL) and product was extracted into CH2Cl2 (2×25 mL). The combined organic layer was washed with brine (20 mL) and dried (Na2SO4). Solvent was evaporated and crude was purified by column chromatography (2 M NH3 in MeOH:CH2Cl2, 1:9) to obtain N-(3-(2-(pyrrolidin-1-yl)ethyl)-1H-indol-5-yl)thiophene-2-carboximidamide (0.39 g, 1.152 mmol, 44.8% yield) as a solid. 1H NMR (DMSO-d6) δ 10.59 (s, 1H), 7.70 (d, 1H, J=2.7 Hz), 7.58 (d, 1H, J=3.9 Hz), 7.26 (d, 1H, J=6.3 Hz), 7.10-7.08 (m, 2H), 6.92 (s, 1H), 6.62 (d, 1H, J=6.3 Hz), 6.23 (s, 2H), 2.80 (t, 2H, J=6.0 Hz), 2.65 (t, 2H, J=5.4 Hz), 2.52-2.48 (m, 4H, merged with DMSO peak), 1.68 (s, 4H); ESI-MS (m/z, %): 339 (MH+, 100).

1. extractionwas extracted into CH2Cl2 (2×25 mL)
2. washThe combined organic layer was washed with brine (20 mL)
3. dry with materialdried (Na2SO4)
4. customSolvent was evaporated
5. customcrude was purified by column chromatography (2 M NH3 in MeOH:CH2Cl2, 1:9)