Sodium Carbonate → Benzo[c][1,8]naphthyridin-6-amine

Participants

Reaction Steps

A solution of tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-ylcarbamate (1.0 eq.) and 2-bromobenzonitrile (1.0 eq.), tetrakis(triphenyl-phosphine)palladium (5 mol %), and 2N aqueous sodium carbonate solution (2.0 eq.) in toluene/ethanol (2:1, 0.03 M) was stirred at 100° C. overnight. After cooling to ambient temperature, the reaction content was diluted with methanol. The insoluble solids were filtered off, and the filtrate was concentrated en vacuo to obtain a crude residue. The crude product was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-80% ethyl acetate in hexane to give benzo[c][1,8]naphthyridin-6-amine as a white solid. 1H NMR (methanol-d4): δ 8.88 (dd, 1H), 8.67-8.63 (m, 2H), 8.30 (d, 1H), 7.90 (dt, 1H), 7.74 (dt, 1H), 7.36 (dd, 1H). LRMS [M+H]=196.1

Provenance & Evidence