1,3-Dibromo-5,5-dimethylhydantoin → HCID 58318609, compound

Participants

Reaction Steps

2-Ethyl-3-phenyl-1,5-naphthyridine (112 mg, 0.43 mmol) and 1,3-dibromo-5,5-dimethylhydantoin (85 mg, 0.7 eq) were suspended in carbon tetrachloride (5 mL). To the mixture was added benzoyl peroxide (10.3 mg, 0.1 eq) and the mixture was heated at reflux for 3 h. To the mixture was added saturated aqueous sodium bicarbonate solution (3 mL). The layers were separated and the aqueous layer was extracted with CH2CH2 (3 mL×2). The combined organic layers were washed with brine (3 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure to give an orange syrup. The material is used as such for the next step. LC-MS (ESI) m/z 314 [M+H]+. A mixture of 2-(1-bromoethyl)-3-phenyl-1,5-naphthyridine (120 mg, 0.38 mmol) in DMF (2.0 mL) was treated with phthalimide potassium salt (142 mg, 2.0 eq) at 60° C. for 2 h. LCMS showed completion. The reaction mixture was partitioned between water and EtOAc, worked up and purified by silica gel column chromatography using EtOAc-hexane (0/1 to 2/1) as eluent to give a white solid. 1H NMR (500 MHz, CDCl3) δ ppm 8.88 (1H, dd, J=5.0, 1.6 Hz), 8.31 (1H, J=10 Hz), 8.1 (1H, s), 7.63-7.54 (5H, m), 7.27-7.17 (8H, m), 5.88 (1H, dd, J=10, 5.0 Hz), 1.76 (3 H, J=10 Hz); LC-MS (ESI) m/z 380 [M+H]+.

Provenance & Evidence