Methyl 7-methyl-alpha-oxo-1H-indole-3-acetate → 3-(7-Methyl-1H-indol-3-yl)-4-[2-methyl-5-(4-methyl-piperazin-1-yl)-pyridin-3-yl]-pyrrole-2,5-dione

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-[5-(4-Methyl-piperazin-1-yl)-2-nitro-pyridin-3-yl]-acetamide (96 mg, 0.34 mmol) and (7-Methyl-1H-indol-3-yl)-oxo-acetic acid methyl ester (127 mg, 0.58 mmol) in dry THF (8.0 mL) is added at 0° C. under an atmosphere of argon, a solution of 1.0 M KOtBu in THF (1.7 ml, 1.7 mmol). After stirring for 2 h at 0° C., TLC analysis indicated complete consumption of the starting materials. The reaction mixture is diluted with EtOAc and washed with brine. The aqueous phase is extracted with EtOAc and the combined organic layers are washed with brine, dried over Na2SO4, and concentrated at reduced pressure. The residue is purified by FCC (EtOAc/AcOH/H2O 6:1:1) to afford the title compound as an orange powder. 1H NMR (d6-DMSO 400 MHz): δ 2.05 (s, 3H), 2.04-2.11 (m, 4H), 2.46 (s, 3H), 3.06-3.14 (m, 4H), 6.35 (d, J=8.1 Hz, 1H), 6.65 (dd, J=8.1, 7.2 Hz, 1H), 6.84 (d, J=7.2 Hz, 1H), 6.87 (d, J=2.0 Hz,1H), 7.95 (s, 1H), 8.16 (d, J=2.0 Hz, 1H). ES+−MS: 447 [M+H]+.

Provenance & Evidence