Dimethylformamide → HCID 50939344, compound

Participants

Reaction Steps

Under a N2 atmosphere, 6-morpholino-2′,3′,5′,6′-tetrahydrospiro[indoline-3,4′-pyran] (0.216 g, 0.788 mmol) was dissolved in DMF (2.00 mL, 26.0 mmol) and treated with sodium hydride (0.0208 g, 0.867 mmol). The reaction was allowed to stir at rt for 10 minutes and 4-chloro-3-methyl-2-phenylquinoline (0.100 g, 0.394 mmol) was added. The reaction was placed in a preheated oil bath at 140° C. for 6 h. LCMS showed no starting chloroquinoline remained. The reaction was diluted with EtOAc and washed with 2% sodium bicarbonate followed by brine. The organic layer was dried (Na2SO4), filtered and concentrated in vacuo. The crude residue was purified by flash column chromatography eluting with 40% to 60% EtOAc in hexane. The fractions that contained product were further purified by preparative reverse phase chromatography to afford 1-(3-methyl-2-phenyl-4-quinolinyl)-6-(4-morpholinyl)-1,2,2′,3′,5′,6′-hexahydrospiro[indole-3,4′-pyran]. Mass Spectrum (ESI) m/e=492.3 (M+1) 1H NMR (500 MHz, DMSO-d6) δ ppm 8.06-8.10 (1H, m), 7.80-7.84 (1H, m), 7.74 (1H, ddd, J=8.4, 6.8, 1.5 Hz), 7.64-7.69 (2H, m), 7.48-7.59 (4H, m), 7.11 (1H, d, J=8.3 Hz), 6.27 (1H, dd, J=8.3, 2.2 Hz), 5.58 (1H, d, J=2.2 Hz), 4.01 (1H, d, J=9.8 Hz), 3.83-3.97 (3H, m), 3.56-3.63 (4H, m), 3.48 (2H, tt, J=12.0, 2.1 Hz), 2.82-2.91 (4H, m), 2.22 (3H, s), 1.93-2.05 (2H, m), 1.82-1.88 (1H, m), 1.65-1.73 (1H, m)

Provenance & Evidence