Sodium hydride → HCID 57586716, compound

Participants

Reaction Steps

To a suspension of NaH (24 mg, 1 mmol) in DMF (4 mL) was added 4-bromobenzenethiol (189 mg, 1 mmol) at 0° C. After being stirred at rt for 10 min, a solution of 1-benzyl-4-chloro-1H-[1,8]naphthyridin-2-one (135 mg, 0.5 mmol) in DMF (1 mL) was introduced at rt. The reaction was quenched by adding water followed by extracting with EtOAc. The organic layer was washed with brine and dried over Na2SO4. Column chromatography of the concentrated residue gave 210 mg of product (yield: 100%): 1H NMR (500 MHz, CDCl3) δ 8.63 (d, J=5.0 Hz, 1H), 8.21 (d, J=8.0 Hz, 1H), 7.62 (d, J=8.5 Hz, 2H), 7.46 (d, J=7.5 Hz, 2H), 7.43 (d, J=8.5 Hz, 2H), 7.25 (t, J=7.5 Hz, 2H), 7.21 (dd, J=8.0, 5.0 Hz, 1H), 7.20 (t, J=8.0 Hz, 1H), 6.10 (s, 1H), 5.70 (s, 2H); 13C NMR (125 MHz, CDCl3) 161.65, 150.77, 149.42, 148.87, 137.85, 137.46, 133.78, 132.97, 128.82, 128.47, 127.38, 126.81, 125.50, 118.09, 117.66, 114.65, 44.20; LCMS (EI) m/z 422.8 (M+), 424.8.

Provenance & Evidence