tert-Butyl carbazate → HCID 86722589, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of (E)-2-bromo-4-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-enyl)benzoic acid (800 mg, 1.63 mmol) in DCE (15 mL) was added tert-butyl hydrazinecarboxylate (290 mg, 1.96 mmol), DMAP (218 mg, 1.86 mmol), EDC.HCl (279 mg, 1.86 mmol) and DIPEA (0.8 mL, 4.89 mmol). The reaction mixture was stirred at 25° C. for 12 h, then diluted with water and extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated under reduced pressure. Purification by flash column chromatography (SiO2, 100-200 mesh; eluting with 30% hexane:EtOAc) afforded the title compound as a brown gum (800 mg, 72%): 1H NMR (300 MHz, DMSO-d6) δ 10.5 (bs, 1H), 7.96 (s, 1H), 7.91 (s, 2H), 7.66 (d, J=7.8 Hz, 1H), 7.37 (s, 1H), 7.03 (dd, J=15.3, 8.7 Hz, 1H), 6.78 (d, J=15.9 Hz, 1H), 4.87-4.81 (m, 1H), 3.08 (s, 3H), 1.43 (s, 9H).

Provenance & Evidence