Hydrogen Bromide → HCID 57586731, compound

Participants

Reaction Steps

A mixture of 1-benzyl-4-(4-bromo-phenylsulfanyl)-1H-[1,8]naphthyridin-2-one (200 mg, 0.47 mmol) and HBr (5 mL, 48%) was heated under reflux for 4 h. After cooling, water was added and the mixture was neutralized with NaOH. The mixture was extracted with EtOAc. The organic layer was washed with brine and dried over Na2SO4. After removal of solvent, the solid was recrystallized with EtOAc and hexane to give 30 mg of product (Yield: 19%). Note: the solubility of the product in organic solvent is poor. 1H NMR (500 MHz, DMSO-d6) δ 12.12 (s, 1H), 8.58 (d, J=4.0 Hz, 1H), 8.22 (d, J=8.0 Hz, 1H), 7.76 (d, J=8.0 Hz, 2H), 7.58 (d, J=8.0 Hz, 2H), 7.29 (dd, J=8.0, 5.0 Hz, 1H), 5.74 (s, 1H); LCMS (EI) m/z 332.8 (M+), 334.9.

Provenance & Evidence