Chlorosuccinimide → HCID 10293010, compound

Participants

Reaction Steps

To a stirred solution of 7-cyano-5-isopropoxymethyl-5-(1,1-difluoroethyl)-5,10-dihydrobenzo[b][1,8]naphthyridine (22)(2.184 g, 6.361 mmol) in anhydrous 1:4 i-PrOH-MeCN (35 mL) at room temperature was added NCS (1.040 g, 7.633 mmol). The reaction mixture was heated to reflux for 2 h 40 min. The reaction was quenched with saturated aqueous NaHCO3 (100 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) afforded 23 (2.021 g, 84% yield) as a pale yellow solid: m.p. 79-81° C.; low resolution mass spectrum (ESI) m/z 378.3 [(M+H)+ calcd for C19H19ClF2N3O: 378.12].

Provenance & Evidence