Trifluoroacetic acid → 3-(1-Benzenesulfonyl-1H-indol-5-yl)-N-hydroxy-acrylamide

Participants

Reaction Steps

NH2OTHP (0.43 g, 3.67 mmol) was added to a solution of 8 (1.00 g, 3.05 mmol), PyBOP (1.69 g, 3.24 mmol), and triethylamine (1.02 ml, 7.33 mmol) in DMF (1.5 mL). The reaction mixture was stirred at room temperature for 3 h before it was quenched with water and extracted with EtOAc (20 mL×3). The combined organic layer was dried over anhydrous MgSO4 and concentrated under reduced pressure. The residue was purified by silica gel chromatography (CH2Cl2:CH3OH=30:1:1% NH3(aq)) to give a white solid, which was treated with TFA (6.90 ml, 92.90 mmol) in the presence of CH3OH (140 mL). The reaction mixture was stirred overnight at room temperature. Then the mixture was concentrated under reduced pressure to give a white residue, which was recrystallized by CH3OH to afford Compound 3 (0.85 g) as a red solid. 1H NMR (500 MHz, CDCl3): δ6.42 (d, J=15.8 Hz, 1H), 6.75 (d, J=3.5 Hz, 1H), 7.49-7.54 (m, 3H), 7.59-7.62 (m, 1H), 7.61 (d, J=15.5 Hz, 1H), 7.68 (d, J=3.6 Hz, 1H), 7.72 (s, 1H), 7.93 (d, J=7.7 Hz, 2H), 7.98 (d, J=8.6 Hz, 1H). MS (EI) m/z: 327 (100%), 342 (M+, 3%). HRMS (EI) for C17H14N2O4S (M+): calcd, 342.0674. found, 342.0673.

Provenance & Evidence