反应详情

To a solution of 6-amino-3H-benzo[c][1,2]oxaborol-1-ol (2.98 g, 20 mmol) and NMM in MeCN (150 ml) was added 2-cyano-4-nitrobenzene-1-sulfonyl chloride (5.423 g, 22 mmol) at 0° C., then the solution was stirred at room temperature for overnight. The mixture was concentrated in vacuo at room temperature, and DCM and water was added to the residue. The organic layer was dried over Na2SO4 and concentrated to give the crude product. It was purified by prep. HPLC (column: Luna 300×50.0 mm, 10 u; liquid phase: [A-H2O+0.025% TFA; B-MeCN] B %: 25%-50%, 25 min) to give the title compound (2.0 g, 27.86%) as a yellow solid. 1H NMR: DMSO 400 MHz. δ11.05 (s, 1H), 9.22 (s, 1H), 8.88 (s, 1H), 8.62 (d, J=11.2 Hz, 1H), 8.17 (d, J=8.8 Hz, 1H), 7.45 (s, 1H), 7.31 (d, J=8.0 Hz, 1H), 7.18 (d, J=10.0 Hz, 1H), 4.89 (s, 2H). ESI-MS m/z 360 (M+H, positive); HPLC purity: 93.07% (MaxPlot 190-370 nm), 98.72% (220 nm).

1. concentrationThe mixture was concentrated in vacuo at room temperature
2. additionDCM and water was added to the residue
3. dry with materialThe organic layer was dried over Na2SO4
4. concentrationconcentrated
5. customto give the crude product
6. customIt was purified by prep