Boron tribromide → HCID 72190206, compound

Participants

Reaction Steps

To a solution of Compound 5 (33 mg, 0.058 mmol) in anhydrous DCM (1 mL) was slowly added 1.0 M solution of BBr3 in DCM (23 μL, 0.23 mmol, 4 eq.) via a syringe under N2 at −78° C. After being stirred for 0.5 h, the mixture was quenched by addition of MeOH (0.5 mL) and extracted with DCM (3×10 mL). The combined organic layers were dried over anhydrous MgSO4, filtered and concentrated in vacuum. The residue was purified by column chromatography (silica gel, hexanes: 12% EtOAc) to give Compound 2 (30 mg, 96% yield) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ 11.34 (s, 1H), 10.39 (s, 1H), 9.77 (s, 1H), 7.47 (d, J=8.6 Hz, 1H), 7.43 (dd, J=8.0, 1.7 Hz, 1H), 7.36 (ddd, J=8.8, 7.4, 1.6 Hz, 1H), 7.04 (d, J=2.0 Hz, 1H), 6.95-6.90 (m, 1H), 6.87 (dd, J=8.6, 2.0 Hz, 1H), 6.68 (s, 1H), 6.53 (ddd, J=8.0, 7.3, 1.1 Hz, 1H); HRMS (ESI-TOF) [M+H]+ calcd for C22H12Cl5N2O4 542.9234. found 542.9237; HPLC purity 96.6%.

Provenance & Evidence