Diisopropylethylamine → N-(3-(imidazo[1,2-a]pyridin-2-yl)phenyl)-8-methoxy-2-oxo-2H-chromene-3-carboxamide

Participants

Reaction Steps

Diisopropylethylamine (DIEA, 0.044 mL, 0.25 mmol) was added to 8-methoxy-3-carboxy-coumarin (0.05 g, 0.23 mmol) and O-(7-Azabenzotriazole-1-yl)-N,N,N,N′-tetramethyluronium hexafluorophosphate (HATU, 0.096 g, 0.25 mmol) in 2 mL of dimethylformamide (DMF) with constant stirring at room temperature until a clear solution resulted. Subsequently, 3-Imidazo[1,2-a]pyridin-2-yl-phenylamine (0.048 g, 0.023 mmol) was added and allowed to react for approximately 30 minutes, when a yellow solid precipitated out of solution. The precipitate was filtered and dried under suction and then in vacuo to give 1541: 1H NMR (400 MHz, DMSO-d6) δ 10.78 (s, 1H), 8.92 (s, 1H), 8.54 (d, J=7.0 Hz, 1H), 8.44 (s, 1H), 8.31 (s, 1H), 7.73 (m, 2H), 7.60 (d, J=9.0 Hz, 1H), 7.57 (d, J=9.0 Hz, 1H), 7.44 (m, 3H), 7.26 (dd, J=5.5, 6.8 Hz, 1H), 6.90 (dd, J=5.5, 6.8 Hz, 1H), 3.96 (s, 3H); LCMS (ESI) m/z 412 (MH+).

Provenance & Evidence