HCID 18187295, compound → HCID 18187362, compound

Participants

Reaction Conditions

Reaction Steps

Method GG: A solution of 7-chloro-9-difluoromethyl-4-azaacridine (396 mg 1.5 mmol) in THF (10 mL) was cooled under N2 to −78° C. n-Butyl lithium was added dropwise over 15 min and the reaction mixture was stirred at −78° C. for 5 h. The reaction was quenched with sat. NH4Cl solution and extracted with EtOAc (3×20 mL). The combined organic layers were washed with brine, dried and concentrated. Column chromatography (SiO2, 10% EtOAc-hexane-1% Et3N) afforded the desired material 5-Butyl-7-chloro-5-difluoromethyl-5,10-dihydro-benzo[b][1,8]naphthyridine as a viscous yellow oil (10 mg, 2.1%).

Provenance & Evidence