Methyl iodide → HCID 86710411, compound

Participants

Reaction Conditions

Reaction Steps

(S)-tert-Butyl (1-((9-cyano-4,6-dimethyl-5-oxo-5,6-dihydrobenzo[c][2,7]naphthyridin-8-yl)oxy)-4-methylpentan-2-yl)carbamate (60 mg, 0.129 mmol), prepared as described in Example 64, Part B, was taken in DMF (3 mL) and cooled to 0° C. The reaction mixture was treated with NaH (10.33 mg, 0.258 mmol) followed by MeI (0.016 mL, 0.258 mmol). After stirring at 0° C. for 10 min, the reaction mixture was warmed to room temperature and stirred overnight. The mixture was then quenched with ice-cold water and extracted with ethyl acetate (2×3 mL). The combined organic layers were dried with sodium sulfate and concentrated under reduced pressure to afford (S)-tert-butyl (1-((9-cyano-4,6-dimethyl-5-oxo-5,6-dihydrobenzo[c][2,7]naphthyridin-8-yl)oxy)-4-methylpentan-2-yl)(methyl)carbamate (70 mg, 0.127 mmol, 99% crude yield) as an off-white solid. The material was carried forward without further purification. LC/MS (ESI) m/e 479.2 [(M+H)+, calcd for C27H35N4O4 479.3]; LC/MS retention time (method C): tR=2.16 min.

Provenance & Evidence