2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 59409005, compound

Participants

Reaction Steps

A solution of 3-(5-bromo-1H-indol-3-yl)-4-(1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-8-yl)-pyrrole-2,5-dione (300 mg, 0.668 mmol) in anhydrous tetrahydrofuran (15 ml) at room temperature was treated with 2,3-dichloro-5,6-dicyano-p-benzoquinone (182 mg, 0.802 mmol) and stirred for 30 minutes. The reaction was treated with 10% aqueous sodium sulfite (40 ml) and diluted with water (50 ml) and ethyl acetate (50 ml). The aqueous layer was removed and the organic layer was washed with saturated aqueous sodium bicarbonate (50 ml) then water (2×50 ml). The organic layer was dried over anhydrous sodium sulfate and evaporated to dryness. The residue was purified by flash column chromatography (SiO2, 1% methanol to 10% methanol in dichloromethane) to provide 3-(5-bromo-1H-indol-3-yl)-4-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-8-yl)-pyrrole-2,5-dione as an orange solid (255 mg). 400 MHz 1H NMR (DMSO-d6) δ: 11.94 (s, 1H), 10.95 (s, 1H), 7.99 (s, 1H), 7.45 (d, J=1.6 Hz, 1H), 7.33 (m, 2H), 7.08 (dd, J=6.8 and 1.6 Hz, 1H), 6.81 (d, J=1.6 Hz, 1H), 6.34 (d, J=2.8 Hz, 1H), 6.20 (d, J=2.0 Hz, 2H), 4.17 (m, 2H), 2.75 (m, 2H), 2.12 (m, 2H); LCMS: 446 and 448 [M+H].

Provenance & Evidence