Pyridine → (Z)-2,2,2-trifluoro-N-(4-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)-3-((2-oxodihydrofuran-3(2H)-ylidene)methyl)phenyl)acetamide

Participants

Reaction Steps

The crude intermediate (Z)-2-((2-oxodihydrofuran-3(2H)-ylidene)methyl)-4-(2,2,2-trifluoroacetamido)benzene-1-sulfonyl chloride (2.85 g, 10 mmol) and 6-aminobenzo[c][1,2]oxaborol-1(3H)-ol (1.5 g, 10 mmol) was suspended in CAN (50 ml), followed by the addition of pyridine (3 ml) dropwise. After stirred at rt for 3 hrs, the mixture was poured into ice-H2O and extracted with EtOAc, washed with H2O, brine, dried over MgSO4, filtered, concentrated in reduced pressure to dryness. The crude product was treated with DCM to give (Z)-2,2,2-trifluoro-N-(4-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)-3-((2-oxodihydrofuran-3(2H)-ylidene)methyl)phenyl)acetamide as a solid (3.4 g). 1H NMR (400 MHz, DMSO-d6) δ (ppm): 11.63 (s, 1H), 10.34 (s, 1H), 9.18 (s, 1H), 8.00 (d, J=8.4 Hz, 1H), 7.87 (s, 1H), 7.87 (dd, J=8.4, 1.6 Hz, 1H), 7.82 (t, J=2.8 Hz, 1H), 7.34 (d, J=1.6 Hz, 1H), 7.21 (d, J=8.4 Hz, 1H), 7.07 (dd, J=8.4, 1.6 Hz, 1H), 4.85 (s, 2H), 4.28 (t, J=7.2 Hz, 2H), 2.88 (dt, J=2.8, 7.2 Hz, 2H). MS (ESI) m/z=495 (M−1).

Provenance & Evidence