3-Aminoquinoline → HCID 10406058, compound

Participants

Reaction Steps

A solution of 1-pentyl-1H-indole-5-carboxylic acid (0.687, 2.97 mmol), O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluorophospate (HBTU) (1.18 g, 3.11 mmol) and N,N-diisopropylethyl (1.14 mL, 6.53 mmol) in acetonitrile (20 mL) was stirred at ambient temperature for 5 minutes. Quinolin-3-ylamine (1.93 g, 13.4 mmol) was added, and the solution was heated at reflux for 18 hours. The solvent was evaporated in vacuo, and the residue was partitioned between dichloromethane and water. The product was preabsorbed onto silica gel and purified by flash chromatography using ethyl acetate in hexane as the eluant, to give the product, 0.40 g (38%). MS: m/z 358 (MH+). 1H NMR (DMSO-d6): 0.84 (t, 3 H), 1.23-1.34 (m, 4 H), 1.73-1.83 (m, 2 H), 4.24 (t, 2 H), 6.64 (d, 1 H), 7.53 (d, 1 H), 7.56-7.69 (m, 3 H), 7.86 (d, 1 H), 7.98 (t, 2 H), 8.37 (s, 1 H), 8.89 (d, 1 H), 9.21 (d, 1 H) and 10.60 (s, 1 H).

Provenance & Evidence