Boron tribromide → HCID 67450398, compound

Participants

Reaction Steps

Following General Procedure F, (R)-tert-butyl 2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl(methyl)carbamate (2.20 g, 4.60 mmol) was treated with BBr3 (1.0 M in CH2Cl2, 50 mL, 50 mmol) to afford the desired product as a yellow solid (1.50 g, 73%): 1H NMR (500 MHz, CD3OD) δ 7.58 (d, J=5.4 Hz, 1H), 7.55 (dd, J=7.9, 1.8 Hz, 1H), 7.45 (dd, J=7.8, 1.9 Hz, 1H), 7.35 (dd, J=7.9, 1.7 Hz, 1H), 7.30 (dd, J=7.7, 1.6 Hz, 1H), 7.08 (d, J=0.8 Hz, 1H), 6.17 (d, J=5.4 Hz, 1H), 3.36-3.19 (m, 3H), 2.57 (d, J=0.6 Hz, 3H), 1.50 (d, J=6.4 Hz, 3H); ESI MS m/z 365 [C21H20N2O2S+H]+; HPLC 98.3% (AUC), tR=8.64 min.

Provenance & Evidence