6-Bromo-1-(6-chloro-7-methoxy-2,3-dimethylquinolin-4-yl)-2',3',5',6'-tetrahydrospiro[indoline-3,4'-pyran] → HCID 67285125, compound

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Reaction Conditions

Reaction Steps

A mixture of 6-bromo-1-(6-chloro-7-methoxy-2,3-dimethylquinolin-4-yl)-2′,3′,5′,6′-tetrahydrospiro[indoline-3,4′-pyran] (0.1 g, 0.205 mmol) and CuCN (0.0367 g, 0.41 mmol) in DMF (1 mL) was stirred at 150° C. After 48 h, the mixture was concentrated under reduced pressure. The residue was purified by column chromatography on a silica gel column using 0 to 100% gradient of EtOAc in hexane as eluent to give 1-(6-chloro-7-methoxy-2,3-dimethyl-4-quinolinyl)-1,2,2′,3′,5′,6′-hexahydrospiro[indole-3,4′-pyran]-6-carbonitrile. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.67 (1H, s), 7.59 (1H, s), 7.47 (1H, d, J=7.4 Hz), 7.12 (1H, dd, J=7.6, 1.4 Hz), 6.16 (1H, d, J=1.6 Hz), 4.10 (1H, d, J=9.8 Hz), 4.00 (3H, s), 3.82-3.94 (3H, m), 3.42-3.56 (2H, m), 2.66 (3H, s), 2.15 (3H, s), 1.98-2.11 (2H, m), 1.89 (1H, dd, J=13.7, 1.6 Hz), 1.74 (1H, dd, J=13.5, 1.0 Hz); Mass Spectrum (ESI) m/e=434.2 (M+1).

Provenance & Evidence