4-Toluenesulfonyl chloride → 7-iodo-1,5-naphthyridin-2(1H)-one

Participants

Reaction Steps

To a solution of 7-iodo-1,5-naphthyridine 1-oxide (D-15) (1.570 g, 5.77 mmol, 1.0 eq) in chloroform (30 mL), p-toluenesulfonyl chloride (1.210 g, 6.35 mmol, 1.1 eq), potassium carbonate (2.711 g, 19.5 mmol, 3.4 eq) and water (10 mL) were added. After stirring at RT for 16 h, the reaction mixture was diluted with water (50 mL), filtered to obtain the desired product 7-iodo-1,5-naphthyridin-2(1H)-one (D-16) (740 mg, 47.1%) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ: 8.60 (s, 1H), 7.98 (d, J=1.8 Hz, 1H), 7.85 (d, J=9.9 Hz, 1H), 6.72 (d, J=9.9 Hz, 1H); ESI-MS m/z: 272.97 [M+H]+.

Provenance & Evidence