Boron tribromide → HCID 16741729, compound

Participants

Reaction Steps

To a solution of 3-benzofuran-3-yl-4-(5-benzyloxy-1-methyl-1H-indol-3-yl)-pyrrole-2,5-dione (31) (22 mg, 0.044 mmol) in 2 ml of dry dichloromethane was added dropwise boron tribromide (44 mg, 0.178 mmol) at −10° C. After 45 min, the reaction was quenched with saturated NaHCO3, and diluted with ethyl acetate. The organic layer was separated, dried over anhydrous Na2SO4 and concentrated. The residue was purified by preparative TLC (ethyl acetate:hexane; 2:3) to afford product (11 mg, 68%). 1H NMR (DMSO-d6, 400 MHz) 3.81 (s, 3H), 6.21 (d, J=2.1 Hz, 1H), 6.59 (dd, J=2.2, 8.5 Hz, 1H), 6.96 (m, 2H), 7.18 (m, 2H), 7.60 (d, J=8.5 Hz, 1H), 7.86 (s, 1H), 8.23 (s, 1H), 8.67 (s, 1H), 11.12 (s, 1H); 13C NMR (DMSO-d6, 100 MHz) 14.5, 103.6, 106.1, 111.2, 111.8, 111.9, 112.5, 121.1, 122.2, 123.0, 125.0, 126.1, 127.0, 131.6, 133.2, 134.9, 147.3, 152.1, 154.6, 172.4, 172.7. FAB-HRMS calcd for C21H14N2O4+Na+: 381.0846; found: 381.0844.

Provenance & Evidence