Boron tribromide → N-[4-(4-fluoro-phenyl)-5-(4-nitro-benzyl)-thiazol-2-yl]-3,4-dihydroxy-benzamide

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Reaction Steps

A procedure similar to that in Example 7 was used. N-[4-(4-fluoro-phenyl)-5-(4-nitro-benzyl)-thiazol-2-yl]-3,4-dimethoxy-benzamide prepared in Example 20 and boron tribromide were used as starting materials. The obtained crude product was recrystallized with acetone to give a product as a pale yellow solid in a yield of 63.3%, mp: 276-278 └(Dec). 1H-NMR (DMSO-d6, 400 MHz) δ: 4.41 (2H, s, CH2), 6.81 (1H, d, J=8.12 Hz, ArH), 7.29 (2H, t, 3JFH=3JHH=8.96 Hz, ArH), 7.47˜7.54 (4H, m, ArH), 7.67 (2H, dd, 3JHH=8.68 Hz, 4JFH=5.60 Hz, ArH), 8.20 (2H, d, J=8.40 Hz, ArH), 9.32 (1H, br, OH), 9.81 (1H, br, OH), 12.38 (1H, br, CONH); EI-MS m/e (%): 465.0 (M+, 28), 329.0 (100); HREI-MS Calcd. for C23H16FN3O5S: 465.0795. found: 465.0798.

Provenance & Evidence