4-Bromopyrazole → 4-[(benzyloxy)methyl]-5-[(4-bromo-1H-pyrazol-1-yl)methyl]-1,3-oxazolidin-2-one

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-bromo-1H-pyrazole (2.33 g, 15.9 mmol), 4-[(benzyloxy)methyl]-5-(iodomethyl)-1,3-oxazolidin-2-one (5.00 g, 14.4 mmol), and potassium phosphate tribasic (9.17 g, 43.3 mmol) in DMF (50 mL) was stirred and heated to 90° C. for 16 hours. The reaction mixture was cooled to ambient temperature, diluted with water, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford the crude product residue. The crude product residue was purified by reverse phase HPLC to afford 4-[(benzyloxy)methyl]-5-[(4-bromo-1H-pyrazol-1-yl)methyl]-1,3-oxazolidin-2-one. MS ESI calc'd. for C15H12BrN3O3 [M+H]+ 366 and 368. found 366 and 368. 1H NMR (400 MHz, DMSO-d6) δ 7.99 (s, 1H), 7.88 (s, 1H), 7.60 (s, 1H), 7.38-7.29 (m, 5H), 4.63-4.60 (m, 1H), 4.54 (s, 2H), 4.39 (d, J=5.6 Hz, 2H), 3.80-3.76 (m, 1H), 3.41 (d, J=4.8 Hz, 2H).

Provenance & Evidence