Potassium Carbonate → 8-chloro-9-methoxy-4,6-dimethylbenzo[c][2,7]naphthyridin-5(6H)-one

Participants

Reaction Conditions

Reaction Steps

A mixture of 9-bromo-8-chloro-4,6-dimethylbenzo[c][2,7]naphthyridin-5(6H)-one (0.05 g, 0.148 mmol), copper(I)iodide (0.031 g, 0.163 mmol), L-proline (0.020 g, 0.178 mmol), sodium methoxide (0.040 g, 0.741 mmol) and K2CO3 (0.041 g, 0.296 mmol) were stirred in DMSO (1.5 mL). The mixture was heated to 80° C. for 16 h. After cooling, the crude reaction mixture was diluted with methanol, filtered through diatomaceous earth (Celite®) and concentrated under reduced pressure to afford 8-chloro-9-methoxy-4,6-dimethylbenzo[c][2,7]naphthyridin-5(6H)-one, as brown solid (40 mg). LC/MS (ESI) m/e 289.0 [(M)+, calcd for C15H14ClN2O2, 289.1]; LC/MS retention time (method D): tR=0.89 min.

Provenance & Evidence