Pyridine → 4'-(Methylsulfonamido)-5,6,7-trimethoxyflavone

Participants

Reaction Conditions

Reaction Steps

The aminoflavone 10a (0.13 g, 0.40 mmol) was dissolved in 5 mL of dry methylene chloride, then 2 mL of freshly distilled pyridine was added. The solution was cooled to 0° C. then was dropwise added freshly distilled methanesulfonyl chloride (0.6 mmol). The reaction mixture was stirred at 0° C. for 1 h and at room temperature for an additional hour, then poured into 30 mL saturated NaHCO3. The resulting mixture was extracted with methylene chloride. The combined organic layers were washed with 5% HCl to remove pyridine, dried over Na2SO4 and concentrated. The residue was purified by column chromatography on silica gel (acetone:toluene=1:5) to give 10e (0.12 g, 74%). 1H NMR (400 MHz, Acetone) δ 3.11 (s, 3H), 3.81 (s, 3H), 3.87 (s, 3H), 4.00 (s, 3H), 6.60 (s, 1H), 7.11 (s, 1H), 7.50 (d, J=8.8 Hz, 2H), 8.02 (d, J=8.8 Hz, 2H).

Provenance & Evidence