Boron tribromide → HCID 178426230, compound

Participants

Reaction Steps

Reaction of 165a (0.075 g, 0.203 mmol) and 1M BBr3 (0.24 mL) in CH2Cl2 (8 mL) within 48 h as described for the synthesis of 148a gave compound 167a (0.042 g, 62%) as olive green solid. 1H NMR (400 MHz, CD3OD) δ 8.18 (s, 1H), 7.66 (d, J=8.0 Hz, 2H), 7.55 (d, J=5.7 Hz, 1H), 7.20 (d, J=7.7 Hz, 2H), 6.97 (d, J=6.7 Hz, 1H), 4.55 (m, 2H), 4.43 (t, J=6.7 Hz, 2H), 2.34 (s, 3H), 2.01 (m, 4H), 1.39 (t, J=22.5 Hz, 2H). 13C NMR (100 MHz, CD3OD) δ 149.25, 139.68, 130.93, 129.13, 127.01, 122.27, 51.41, 30.95, 24.51, 21.83. HRMS (EI) calcd for C19H22N4OS [M]+ 354.151. found 354.1512.

Provenance & Evidence