N-bromobutanimide → HCID 53466341, compound

Participants

Reaction Steps

A sample of NBS (299 mg, 1.68 mmol) was added to a solution of 7-(2-Chloro-6-fluorophenyl)-5-(4-chlorophenyl)-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine (3a) (101 mg, 0.28 mmol) in isopropanol (5 mL). The reaction mixture was refluxed for 36 h, then cooled to room temperature, treated with saturated NaHCO3 solution (20 mL) and extracted with EtOAc (15 mL×3). The combined organic layer was dried over Na2SO4 and evaporated under reduced pressure. The given residue was purified through silica gel column chromatography (EtOAc/Hexanes 30:70) to afford a 42 mg white solid of 4a in 42% yield. m.p. 238-239° C. Rf=0.33 (EtOAc/Hexanes 30:70). MS: MH+=359. 1H NMR (500 MHz, CDCl3): δ 8.48 (s, 1H, CHar), 8.15 (d, J=7.5 Hz, 2H, CHar), 7.57-7.39 (m, 5H, CHar), 7.20-7.19 (m, 1H, CHar). HPLC: 97.9% (Method C, tR=5.47 min).

Provenance & Evidence