Pyridine → N-(3-bromo-4-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)phenyl)-2,2,2-trifluoroacetamide

Participants

Reaction Steps

Pyridine (1.5 equiv) was added dropwise to the cooled suspension of the crude 2-bromo-4-(2,2,2-trifluoroacetamido)benzene-1-sulfonyl chloride (24 g, 0.06 mol) and 6-aminobenzo[c][1,2]oxaborol-1(3H)-ol (1.2 eq) in acetonitrile (300 ml) at 0° C. over 10 min. The r×n mix was stirred overnight. The solid was filtered and washed with EtOAc. The filtrate was washed with, H2O, brine, dried over MgSO4, filtered, and concentrated to dryness to give crude N-(3-bromo-4-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)phenyl)-2,2,2-trifluoroacetamide which was purified by flash chromatography on silica gel. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 11.6 (s, 1H), 10.56 (s, 1H), 9.20 (s, 1H), 8.12 (d, J=1.9 Hz, 1H), 8.06 (d, J=8.8 Hz, 1H), 7.79 (dd, J=2.0, 8.6 Hz, 1H), 7.47 (d, J=1.8 Hz, 1H), 7.24 (d, J=8.4 Hz, 1H), 7.20 (dd, J=1.9, 8.3 Hz, 1H), 4.85 (s, 2H). MS (ESI) m/z=479 (M+1).

Provenance & Evidence