Sodium Carbonate → Methyl 5-aminobenzo[f][1,7]naphthyridine-8-carboxylate

Participants

Reaction Steps

A solution of 2-(tert-butoxycarbonylamino)-4-(methoxycarbonyl) phenylboronic acid (from the previous step) (1.0 eq.) and 3-bromopicolinonitrile (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 mixture was filtered to collect the precipitate. The precipitate was rinsed with EtOAc to give methyl 5-aminobenzo[f][1,7]naphthyridine-8-carboxylate as a pale brown solid.

Provenance & Evidence