Boron tribromide → HCID 58102874, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of N-(4-bromophenyl)-1-(4-methoxy-2,3-dihydro-1H-inden-1-yl)-2-oxo-1,2-dihydropyridine-3-carboxamide (0.4 g, 0.91 mmol) in Ch2Cl2 (2 mL) at 0 C was added BBr3 (1M in CH2Cl2, 9 mL). The reaction was stirred at 0° C. for 1 hr. It was poured into sat. aqueous NaHCO3 (50 mL). The mixture was extracted with EtOAc (3×50 mL). The combined organic layers were dried and concentrated to a solid. The solid was washed with MeOH and CH2Cl2 to afford a white solid. It was further purified by prep. HPLC to afford N-(4-bromophenyl)-1-(4-hydroxy-2,3-dihydro-1H-inden-1-yl)-2-oxo-1,2-dihydropyridine-3-carboxamide (120 mg, 31%). Retention time (min)=7.127, method [7], MS (ESI) 425.0 (M+H); 1H NMR (300 MHz, CDCl3) δ 12.19 (s, 1H), 8.61 (dd, J=2.1 Hz, 7.0 Hz, 1H), 7.68 (d, J=9.0 Hz, 2H), 7.47 (d, J=9.0 Hz, 2H), 7.15-7.30 (overlap with CDCl3, 2H), 6.81 (d, J=7.8 Hz, 1H), 6.72 (d, J=7.2 Hz, 1H), 6.60 (dd, J=5.4 Hz, 7.2 Hz, 1H), 6.41 (t, J=7.0 Hz, 1H), 5.0 (br, 1H), 2.80-3.10 (m, 3H), 1.98-2.15 (m, 1H).

Provenance & Evidence