N-methyl-2-pyrrolidone → HCID 70976811, compound

Participants

Reaction Conditions

Reaction Steps

To a flask charged with 1-((2S,4R)-4-amino-6-bromo-2-methyl-3,4-dihydroquinolin-1(2H)-yl)ethanone (for a preparation see Intermediate 1)(2 g, 7.06 mmol) and 2-chloro-5-nitropyridine (2.240 g, 14.13 mmol) was added NMP (10 mL) and the resulting mixture treated with DIPEA (3.70 mL, 21.19 mmol). The mixture was divided between 2 flasks, each flask flushed with nitrogen, sealed and the mixture stirred under microwave irradiation at 200° C. for 2 h. The 2 reaction mixtures were combined, diluted with water and extracted with EtOAc (×4). Combined EtOAc layers were washed with water (×3) then brine, dried over MgSO4 and concentrated in vacuo. The residual brown solid was purified by chromatography eluting with an EtOAc/hexanes gradient, which gave 1-((2S,4R)-6-bromo-2-methyl-4-((5-nitropyridin-2-yl)amino)-3,4-dihydroquinolin-1(2H)-yl)ethanone (4.6 g, 11.35 mmol, 161% yield) as a pale brown foam. LCMS (HpH, 2 min), Rt=1.08 min, MH+=405/407 (doublet).

Provenance & Evidence