6-Bromo-1,2-dihydrospiro(indole-3,4'-oxane) → 6-Bromo-1-(6-chloro-2,3-dimethylquinolin-4-yl)-2',3',5',6'-tetrahydrospiro[indoline-3,4'-pyran]

Participants

Reaction Steps

Prepared according to procedure M using 6-bromo-2′,3′,5′,6′-tetrahydrospiro-[indoline-3,4′-pyran] (0.3 g, 1.12 mmol) and 4,6-dichloro-2,3-dimethylquinoline (0.2783 g, 1.23 mmol) to give 6-bromo-1-(6-chloro-2,3-dimethylquinolin-4-yl)-2′,3′,5′,6′-tetrahydrospiro[indoline-3,4′-pyran] as a brown solid: 1H NMR (500 MHz, DMSO-d6) δ ppm 8.03 (1H, d, J=9.0 Hz), 7.71 (1H, dd, J=8.9, 2.3 Hz), 7.65 (1H, d, J=2.2 Hz), 7.22 (1H, d, J=7.8 Hz), 6.83 (1H, dd, J=7.8, 1.5 Hz), 5.94 (1H, d, J=1.5 Hz), 4.04 (1H, d, J=9.8 Hz), 3.80-3.93 (3H, m), 3.39-3.54 (2H, m), 2.68 (3H, s), 2.22 (3H, s), 1.94-2.06 (2H, m), 1.85 (1H, d, J=13.4 Hz), 1.73 (1H, dd, J=13.4, 1.5 Hz); Mass Spectrum (ESI) m/e=457.1 [M+1 (79Br)] and 459.1 [M+1 (81Br)].

Provenance & Evidence