Sodium Hydroxide → 1-(6-chloro-2,3-dimethyl-4-quinolinyl)-6-(1H-pyrazol-4-yl)-1H-indol-4-ol

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-chloro-4-(4-methoxy-6-(1H-pyrazol-4-yl)-1H-indol-1-yl)-2,3-dimethylquinoline (0.1059 g, 0.272 mmol) in DCM (2.7 mL) in ice bath was added 1M BBr3 in DCM (0.82 mL, 0.815 mmol) dropwise. The mixture was stirred at 0° C. for 1 h and at rt. After 26 h, to the mixture was added ice water and the mixture was neutralized with 10N NaOH to pH 9.0. The resulting solid was filtered to give a brown solid. The brown 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-(6-chloro-2,3-dimethyl-4-quinolinyl)-6-(1H-pyrazol-4-yl)-1H-indol-4-ol as a yellow solid: 1H NMR (500 MHz, DMSO-d6) δ ppm 12.74 (1H, br. s.), 9.74 (1H, s), 8.08 (1H, d, J=8.8 Hz), 7.94 (1H, br. s.), 7.73 (1H, dd, J=8.9, 2.3 Hz), 7.68 (1H, br. s.), 7.33 (1H, d, J=3.4 Hz), 6.94 (1H, d, J=2.2 Hz), 6.87 (1H, d, J=3.2 Hz), 6.76 (1H, s), 6.47 (1H, s), 2.77 (3H, s), 2.06 (3H, s); Mass Spectrum (ESI) m/e=389.0 (M+1).

Provenance & Evidence