Dichloromethane → Trifluoroacetic acid

Participants

Reaction Steps

A solution of tert-butyl 5-{[4-(tert-butoxycarbonyl)-1-piperazinyl]carbonyl}-2-(2-oxo-1,2-dihydro-3-quinolinyl)-1H-indole-1-carboxylate (6-2, 213 mg, 0.373 mmol, 1 equiv) in a 1:1 mixture of CH2Cl2 and trifluoroacetic acid (40 mL) was treated with 3 drops of DMSO and H2O, and the resulting mixture was heated at reflux for 45 minutes. The solution was concentrated, and the residue was dried by azeotropic removal of water using a 90:10 mixture of toluene and methanol (100 mL). It was then purified by reverse phase chromatography (H2O/CH3CN gradient with 0.1% TFA present) to provide 3-[5-(1-piperazinylcarbonyl)-1H-indol-2-yl]-2(1H)-quinolinone (6-3) as a TFA salt (brown solid). 1H NMR (500 MHz, DMSO) δ 12.21 (s, 1H), 11.83 (s, 1H), 8.59 (s, 1H), 7.75 (d, 1H, J=7.9 Hz), 7.74 (s, 1H), 7.59 (d, 1H, J=8.3 Hz), 7.54 (t, 1H, J=7.6 Hz), 7.42 (s, 1H), 7.39 (d, 1H, J=8.3 Hz), 7.25 (m, 2H), 3.86–3.15 (br m, 8H).

Provenance & Evidence