5-Fluoroindole-2-carboxylic acid → 5-fluoro-1H-indole-2-carboxylic acid (3-hydroxy-propyl)-amide

Beteiligte Stoffe

Reaktionsschritte

To a solution of 5-fluoro-1H-indole-2-carboxylic acid (2.27 g, 12.7 mmol) in CH2Cl2 (100 mL) is added DMAP (4.64 g, 38 mmol), EDCI (3.64 g, 19 mmol), 3-amino-propan-1-ol (1.90 g, 25 mmol). The mixture is stirred at room temperature for 24 hours. After the solvent is removed under vacuum, 5% HCl (100 mL) is added to the mixture. It is extracted with EtOAc (100 mL×3). The combined organic layers are washed with saturated aqueous NaHCO3 (100 mL), brine (100 mL) and dried with Na2SO4. Solvent is removed to give 5-fluoro-1H-indole-2-carboxylic acid (3-hydroxy-propyl)-amide; 1H NMR (DMSO-d6) δ 1.69 (quint, 2H, J=6.4 Hz), 3.34 (q, 2H, J=6.0 Hz), 3.48 (t, 2H, J=6.4 Hz), 4.48 (bs, 1H), 6.99-7.10 (m, 2H), 7.36-7.44 (m, 2H), 8.47 (t, 1H, J=5.6 Hz), 11.63 (s, 1H); m/z [M++1] 237.1.

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