Boron tribromide → 9-[4-(Aminomethyl)phenyl]-8-hydroxy-2-methylthieno[2,3-c]quinolin-4(5H)-one

Participants

Reaction Steps

Following General Procedure F, tert-butyl 4-(8-methoxy-2-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzylcarbamate (80 mg, 0.17 mmol) was reacted with tribromoborane (2.0 mL) to afford the desired product (20 mg, 37%) as an off-white solid: 1H NMR (500 MHz, CD3OD) δ 7.63 (d, J=8.9 Hz, 2H), 7.40-7.37 (m, 3H), 7.15 (d, J=8.1 Hz, 1H), 5.76 (s, 1H), 4.28 (s, 2H), 2.33 (s, 3H); ESI MS m/z 337 [C19H16N2O2S+H]+; HPLC >99%, tR=5.91 min.

Provenance & Evidence