Dimethyl Sulfoxide → 8-(cyclopentyloxy)-4-(2,6-dichlorophenylamino)-7-methoxy-2H-chromen-2-one

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (10 mg, 60%, 0.25 mmol) was added to a solution of 2,6-dichloroaniline (40 mg, 0.25 mmol) and anhydrous DMSO (2 mL) at rt under N2. After 40 min, this mixture was added to a solution of 8-(cyclopentyloxy)-7-methoxy-2-oxo-2H-chromen-4-yl 4-methylbenzenesulfonate (70 mg, 0.16 mmol) and anhydrous DMSO (2 mL) at rt under N2. After 1.5 h at rt, the reaction was heated at 50° C. After an additional 1.5 h, a second aliquot of the sodium 2,6-dichloroanilide mixture was added. After an additional hour, the reaction was allowed to cool to rt, diluted with 1M KH2PO4 (40 mL), and extracted with ethyl acetate (40 mL×2). The combined extracts were dried, filtered, concentrated, and purified by silica gel chromatography (4:1→3:2; hexanes:ethyl acetate) to give 8-(cyclopentyloxy)-4-(2,6-dichlorophenylamino)-7-methoxy-2H-chromen-2-one: 1H NMR (400 MHz, DMSO-d6): δ 9.39 (s, 1H), 7.95 (d, 1H), 7.69 (d, 2H), 7.50 (t, 1H), 7.18 (d, 1H), 4.83 (m, 1H), 4.36 (s, 1H), 3.90 (s, 3H), 1.80-1.00 (m, 8H); MS (ESI): 419.9.

Provenance & Evidence