Potassium Carbonate → 8-(5-(1H-1,2,3-triazol-1-yl)pentyloxy)-4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2H-chromen-2-one

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Reaction Steps

Potassium carbonate (350 mg, 2.54 mmol) was added to a solution of 8-(5-bromopentyloxy)-4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2H-chromen-2-one (1.0 g, 2.0 mmol, Example 28), 1H-1,2,3-triazole (210 mg, 3.04 mmol), and DMF (15 mL) at rt. After 3.5 h at 80° C., the mixture was allowed to cool to rt, quenched with water (10 mL), and then extracted with ethyl acetate (20 mL×3). The combined extracts were washed with brine, dried, filtered, concentrated, and then purified by silica gel chromatography (dichloromethane:methanol) to give 8-(5-(1H-1,2,3-triazol-1-yl)pentyloxy)-4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2H-chromen-2-one: 1H NMR (400 MHz, DMSO-d6): δ 9.52 (s, 1H), 8.81 (s, 2H), 8.13 (s, 1H), 7.94 (d, 1H), 7.69 (s, 1H), 7.19 (d, 1H), 4.63 (s, 1H), 4.40 (t, 2H), 3.97 (t, 2H), 3.90 (s, 3H), 1.88 (m, 2H), 1.75 (m, 2H), 1.45 (m, 2H); MS (ESI): 490.0.

Provenance & Evidence