Sodium bis(trimethylsilyl)amide → Methyl 5-oxo-5,6-dihydrobenzo[c][2,6]naphthyridine-7-carboxylate

Participants

Reaction Steps

Methyl 2-amino-3-(4-(diisopropylcarbamoyl)pyridin-3-yl)benzoate (1.0 eq, 244 mg, 0.686 mmol) was dissolved under nitrogen atmosphere in anhydrous THF (1.5 ml). A NaHMDS solution (1.0 M in THF, 2.0 eq, 1.4 ml, 1.4 mmol) was added dropwise through syringe. The resulting suspension was stirred at room temperature for 1 hour. The reaction was quenched by addition of a saturated aqueous solution of ammonium chloride. The solid that formed was filtered and dried. After trituration in methanol and filtration, methyl 5-oxo-5,6-dihydrobenzo[c][2,6]naphthyridine-7-carboxylate was isolated as a grey fluffy solid (93 mg, 53% yield). LCMS (ES): >95% pure, m/z 255 [M+1]+.

Provenance & Evidence