Sodium hydride → (S)-tert-butyl (4-methyl-1-((5-oxo-5,6-dihydrobenzo[c][2,7]naphthyridin-8-yl)oxy)pentan-2-yl)carbamate

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (5.56 mg, 0.232 mmol, 60% in mineral oil) was taken in tetrahydrofuran (1 mL) and cooled to 0° C. The suspension was treated with (S)-tert-butyl (1-(4-(3-carbamoylpyridin-4-yl)-3-fluorophenoxy)-4-methylpentan-2-yl)carbamate (50 mg, 0.116 mmol) in THF (1 mL) dropwise and the temperature was maintained at 0° C. for 30 min. The reaction mixture was then allowed to warm to room temperature and stirred for 2 h. The reaction was quenched with ice and extracted with ethyl acetate (3×5 mL). The combined organic layers were washed with brine (1×5 mL), dried (Na2SO4) and concentrated under reduced pressure to afford (S)-tert-butyl (4-methyl-1-((5-oxo-5,6-dihydrobenzo[c][2,7]naphthyridin-8-yl)oxy)pentan-2-yl)carbamate (40 mg, 0.097 mmol, 84% yield) as a colorless solid. LC/MS (ESI) m/e 412.2 [(M+H)+, calcd for C23H30N3O4 412.2]; LC/MS retention time (method C): tR=1.97 min.

Provenance & Evidence