Potassium Carbonate → HCID 136158594, compound

Participants

Reaction Steps

Carbonic acid 9-benzhydryloxy-7-(4-fluoro-benzyl)-6,8-dioxo-7,8-dihydro-6H-pyrrolo[3,4-g]quinoxalin-5-yl ester ethyl ester 244 (500 mg, 0.87 mmol) was dissolved in THF (9 mL, 0.1 M) along with DMAP (211 mg, 1.73 mmol, 2 equiv.). A solution of K2CO3 (1.20 g, 8.66 mmol, and 10 equiv.) was dissolved separately in H2O (6 mL) before being transferred to the reaction mixture. The reaction was allowed to stir for 18 hours and quenched with HCl (20 mL, 1 N) and extracted with ethyl acetate (2×30 mL). The organic layer was washed with saturated NH4Cl solution (25 mL), brine solution (25 mL) and dried over Na2SO4 and concentrated in vacuo to yield 5-benzhydryloxy-7-(4-fluoro-benzyl)-9-hydroxy-pyrrolo[3,4-g]quinoxaline-6,8-dione 245 (94%, 413 mg, 0.82 mmol). 1H NMR (300 MHz) CDCl3 δ 9.08 (d, J=1.5 Hz, 1 H), 8.92 (d, J=1.5 Hz, 1H), 7.67 (s, 1 H), 7.67-7.42 (dd, J1=1.5 Hz, J2=8.4 Hz, 4 H), 7.43-7.48 (m, 2 H), 7.19-7.27 (m, 7 H), 7.03-7.20 (m, 1 H), 4.86 (s, 2 H). MS: 528.0 (M+23). TLC Rf: 0.2 Hexanes/Ethyl acetate (8/2)

Provenance & Evidence