Bromoacetyl bromide → HCID 59504686, compound

Participants

Reaction Steps

To a solution of 4-{5-[5-methyl-1-(4-methylbenzyl)-1H-pyrazol-3-yl]-1,2,4-oxadiazol-3-yl}-aniline (Step 1, 150 mg, 0.434 mmol) and N,N-diisopropylethylamine (113 μL, 0.651 mmol) in dichloromethane (5 mL) was added bromoacetyl bromide (46 μL, 0.521 mmol) dropwise at a temperature of 0° C. After 5 minutes, the reaction mixture was allowed to warm to rt. After a further 2 h, the reaction mixture was diluted with an equal volume of dichloromethane, and 20 mL water were added. After separation of the organic from the aqueous layer, the organic phase was dried over anhydrous sodium sulfate. Subsequent filtration and evaporation of the solvent yielded the title compound which was obtained in pure form after stirring with cyclohexane (195 mg, 96%): 1H NMR (400 MHz, DMSO-d6) 10.70 (s, 1H), 8.03 (d, 2H), 7.80 (d, 2H), 7.18 (d, 2H), 7.10 (d, 2H), 6.90 (s, 1H), 5.44 (s, 2H), 4.09 (s, 2H), 2.32 (s, 3H), 2.28 (s, 3H); ES-MS m/z 466/468, HPLC RT (Method F) 2.45 min.

Provenance & Evidence