Potassium tert-butoxide → HCID 86643471, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (±)-cis-3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-8-yl)-4-(1H-indol-3-yl)-pyrrolidine-2,5-dione (760 mg, 2.06 mmol) in anhydrous tetrahydrofuran (10 ml) at room temperature was treated with potassium tert-butoxide (1.0 ml, 1.00 mmol; 1M solution in tetrahydrofuran) then heated to 50° C. and stirred for a further 1 hour. The reaction was quenched with water (10 ml) and acidified with 2M hydrochloric acid, and the mixture extracted with dichloromethane (3×50 ml). The combined organic extracts were dried over anhydrous sulfate and evaporated to dryness. The residue was purified by flash column chromatography (SiO2, 1% to 10% methanol in dichloromethane) to provide (±)-trans-3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-8-yl)-4-(1H-indol-3-yl)-pyrrolidine-2,5-dione as an orange solid (46 mg). M.p=141-145° C.; 400 MHz 1H NMR (CDCl3) δ: 8.12 (s, 1H), 8.05 (s, 1H), 7.40 (d, J=8.2 Hz, 1H), 7.29 (s, 1H), 7.23 (m, 1H), 7.11 (m, 2H), 6.78 (s, 1H), 6.39 (d, J=2.7 Hz, 1H), 4.48 (d, J=5.9 Hz, 1H), 4.32 (d, J=5.5 Hz, 1H), 4.16 (t, J=5.5 Hz, 2H), 2.98 (t, J=6.3 Hz, 2H), 2.25 (t, J=6.3 Hz, 2H); LCMS: 370 [M+H].

Provenance & Evidence