Triethylamine → HCID 67285103, compound

Participants

Reaction Steps

A mixture of 1-(6-chloro-2,3-dimethylquinolin-4-yl)-6-morpholino-2′,3′,5′,6′-tetrahydrospiro[indoline-3,4′-pyran] (0.027 g, 0.058 mmol), triethylamine (0.008 mL, 0.058 mmol), and 10% Pd/C (0.02 g, 0.0188 mmol) in MeOH-EtOAc (2:1, 3 mL) was stirred under hydrogen at rt. After 3 h, the mixture was filtered through a Celite™ pad and the pad was washed with MeOH and EtOAc to give a tan solid. The tan solid was purified by column chromatography on a silica gel column using 0 to 100% gradient of EtOAc in hexane as eluent to give 1-(2,3-dimethyl-4-quinolinyl)-6-(4-morpholinyl)-1,2,2′,3′,5′,6′-hexahydrospiro[indole-3,4′-pyran] as a yellow solid: 1H NMR (500 MHz, DMSO-d6) δ ppm 7.97 (1H, d, J=8.3 Hz), 7.71 (1H, d, J=8.1 Hz), 7.62-7.68 (1H, m), 7.42-7.49 (1H, m), 7.08 (1H, d, J=8.3 Hz), 6.23 (1H, dd, J=8.2, 2.1 Hz), 5.41 (1H, d, J=2.2 Hz), 3.77-3.96 (4H, m), 3.52-3.59 (4H, m), 3.41-3.51 (2H, m), 2.81 (4H, dd, J=5.4, 2.9 Hz), 2.68 (3H, s), 2.22 (3H, s), 1.91-2.03 (2H, m), 1.78-1.85 (1H, m), 1.65-1.72 (1H, m); Mass Spectrum (ESI) m/e=430.2 (M+1).

Provenance & Evidence