Trifluoroacetic acid → 9-bromo-6-isopropylbenzo[c]-1,6-naphthyridin-1(2H)-one

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Reaction Steps

To a stirred solution of tert-butyl 2-(9-bromo-1-chlorobenzo[c]-1,6-naphthyridin-6-yl)-2-methylpropanoate (3.32 g, 7.62 mmol) in dichloromethane (30 ml) was added TFA (30 ml). The solution was stirred for 12 hrs, then concentrated to a crude oil. EtOAc was added (20 mL), and the resulting solids were collected by vacuum filtration to afford 9-bromo-6-isopropylbenzo[c]-1,6-naphthyridin-1(2H)-one. The filtrate was concentrated, EtOAc was added, and a second crop of product was obtained by vacuum filtration. 1H NMR (500 MHz, DMSO-D6) δ 11.91 (br d, 1H), 10.28 (d, 1H), 8.41 (d, 1H), 7.89 (dd, 1H), 7.58 (t, 1H), 6.77 (d, 1H), 4.05 (septet, 1H), 1.36 (d, 6H). LRMS (ESI) calc'd for (C15H13BrN2O) [M+H]+, 317.0; found 317.0.

Provenance & Evidence