HCID 18187347, compound → HCID 18187285, compound

Participants

Reaction Steps

Method NNN To a stirred solution 7-chloro-5-(difluoromethyl)-5-diisopropoxymethyl-5,10-dihydrobenzo[b][1,8]naphthyridine (94) (50 mg, 0.13 mmol) in trifluoroacetic acid (2 mL) at room temperature was added borane-methyl sulfide complex (36 μL, 0.38 mmol). After 14 h at room temperature, the reaction mixture was quenched with 1.0 N NaOH and extracted with EtOAc (3×). The combined layers were dried over MgSO4, filtered and concentrated in vacuo. The resulting yellow residue was taken up in MeOH (3 mL), acidified with 4 N HCl in dioxane (100 μL), and stirred at room temperature for 3 hours. The solution was quenched with saturated aqueous NaHCO3 (50 mL) and extracted with EtOAc (3×). The combined organic layers were dried over MgSO4, filtered and concentrated in vacuo. The residue afforded 95 in quantitative yield.

Provenance & Evidence