Acetic Acid → HCID 10138816, compound

Participants

Reaction Steps

A slurry of the 3-{5-[2-oxoethyl]-1H-indol-2-yl}quinolin-2(1H)-one (10-2, 75 mg, 0.25 mmol, 1 equiv) and 1-(methylsulfonyl)piperazine (163 mg, 1.0 mmol, 4 equiv) in 1,2-dichloroethane(100 mL) was treated with acetic acid (0.67 mg, 1.12 mmol, 4.5 equiv) and sodium triacetoxyborohydride (156 mg, 0.75 mmol, 3 equiv) and the reaction was stirred under ambient conditions for 18 hours. The reaction was concentrated and the residue was partitioned between EtOAc and sat. NaHCO3 solution. The organic layer was washed with brine, dried over magnesium sulfate and concentrated. The residue was purified by chromatography on a silica column. Elution with EtOAc to 5% NH3-EtOH/EtOAc gave 3-(5-{2-[4-(methyl-sulfonyl)piperazin-1-yl]ethyl}-1H-indol-2-yl)quinolin-2(1H)-one (10-3) as a yellow solid. 1H NMR (500 MHz, DMSO-d6) δ 12.2 (s, 1H), 11.4 (s, 1H), 8.52 (s, 1H), 7.72 (d, J=8 Hz, 1H), 7.51 (t, J=8 Hz, 1 H), 7.42 (d, J=8 Hz, 1 H), 7.38 (m, 2 H), 7.25 (m, 2H), 6.99 (d, J=8 Hz, 1H), 3.11 (m, 4 H), 3.87 (s, 3H), 2.81 (br t, J=8 Hz, 2 H), 2.61 (br t, J=8 Hz, 2H), 2.56 (m, 4 H).

Provenance & Evidence