N-bromobutanimide → HCID 10113225, compound

Participants

Reaction Steps

To a stirred solution of 7-cyano-5-trifluoromethyl-5-isopropoxymethyl-5,10-dihydrobenzo[b][1,8]naphthyridine (14)(61 mg, 0.176 mmol) in anhydrous acetonitrile (2 mL) at room temperature was added NBS (38 mg, 0.211 mmol). The reaction mixture was stirred at room temperature for 1 h 30 min. The reaction was quenched with 1:1 saturated aqueous NaHCO3/water (20 mL), and extracted with EtOAc (2×). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated in vacuo. Flash chromatography (20%-30% EtOAc-Hexane) furnished 15 (73 mg, 97% yield) as an off-white solid: m.p. 76-77° C.; low resolution mass spectrum (ESI) m/z 426.2 [(M+H)+ calcd for C18H16BrF3N3O: 426.05].

Provenance & Evidence