Methyl iodide → HCID 58928688, compound

Participants

Reaction Steps

Into a flask containing 5-benzhydryloxy-7-(4-fluoro-benzyl)-9-hydroxy-pyrrolo[3,4-g]quinoxaline-6,8-dione 245 (350 mg, 0.69 mmol, 1 equiv.) was added DMF (20 mL) followed by K2CO3 (478 mg, 3.46 mmol, 5 equiv.). To this was added MeI (983 μL, 6.93 mmol, 10 equiv.) under a nitrogen atmosphere and stirred for 16 hours. To the reaction was then added water (50 mL) and extracted with ethyl acetate (2×40 mL). The organic layer was washed several times with water (3×30 mL), saturated NaHCO3 (40 mL), brine solution (30 mL). It was dried over Na2SO4, filtered and concentrated in vacuo before being purified by silica gel chromatography using 3/2 Hexanes/ethyl acetate to obtain 5-benzhydryloxy-7-(4-fluoro-benzyl)-9-methoxy-pyrrolo[3,4-g]quinoxaline-6,8-dione 246 (78%, 280 mg, 0.54 mmol) as a yellow solid. 1H NMR (300 MHz) CDCl3 δ 9.03 (d, J=1.5 Hz, 1 H), 8.97 (d, J=1.5 Hz, 1 H), 7.75 (s, 1 H), 7.60 (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, 1H), 4.86 (s, 2 H), 4.37 (s, 3 H). MS: 542.0 (M+23). TLC Rf: 0.5 Hexanes/Ethyl acetate (1/1)

Provenance & Evidence