4-Chloro-2,3,8-trimethylquinoline → 6-Bromo-1-(2,3,8-trimethylquinolin-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] (0.5 g, 1.86 mmol) and 4-chloro-2,3,8-trimethylquinoline (0.4219 g, 2.05 mmol) to give 6-bromo-1-(2,3,8-trimethylquinolin-4-yl)-2′,3′,5′,6′-tetrahydrospiro[indoline-3,4′-pyran]: 1H NMR (400 MHz, DMSO-d6) δ ppm 7.52 (2H, dd, J=17.2, 7.4 Hz), 7.37 (1H, dd, J=8.2, 7.0 Hz), 7.20 (1H, d, J=7.8 Hz), 6.78 (1H, dd, J=7.8, 1.6 Hz), 5.82 (1H, d, J=2.0 Hz), 3.83-4.00 (4H, m), 3.39-3.54 (2H, m), 2.73 (3H, s), 2.71 (3H, s), 2.24 (3H, s), 1.92-2.10 (2H, m), 1.66-1.90 (2H, m); Mass Spectrum (ESI) m/e=437.0 [M+1 (79Br)] and 439.1 [M+1 (81Br)].

Provenance & Evidence