HCID 67174416, compound → HCID 67311178, compound

Participants

Reaction Conditions

Reaction Steps

Iron powder (0.19 g, 3.30 mmol) was added to a solution of 2-chloro-N-(1-hydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-6-yl)-4-nitro-benzenesulfonamide (0.25 g, 0.67 mmol) in acetic acid (10 mL). The reaction mixture was stirred at 80° C. (bath temp) for 2 h. The mixture was then cooled to rt, and the acetic acid was removed under reduced pressure. The residue was diluted with ethyl acetate (50 mL), the undissolved particulates were removed by filtration through a pad of Celite. The filtrate was washed with water, brine and dried over Na2SO4, decanted and concentrated in vacuo. Purification was accomplished by flash silica gel column chromatography (3% methanol in dichloromethane) followed by dissolving in acidic water (with dilute HCl) and lyophilized provided 48.0 mg (21%) of the title compound as light yellow solid. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 10.10 (s, 1H), 7.63 (d, J=8.9 Hz, 1H), 7.45 (d, J=1.6 Hz, 1H), 7.23 (d, J=8.2 Hz, 1H), 7.19 (dd, J=8.2, 1.9 Hz, 1H), 6.59 (d, J=2.2 Hz, 1H), 6.46 (dd, J=8.6, 2.2 Hz, 1H), 4.85 (s, 2H); MS (ESI) m/z=339 (M+1, positive); HPLC purity: 97.48% (MaxPlot 200-400 nm), 97.96% (220 nm).

Provenance & Evidence