Bromide ion → HCID 12083562, compound

Participants

Reaction Steps

A mixture of 4-[(5-bromo-6-hydroxy-naphthalen-2-ylmethyl)-carbamoyl]-2-phenyl-3-propyl-2H-pyrazol-1-ium; bromide (0.30 g, 0.646 mmol), prepared in the previous step, bromoacetonitrile (0.054 mL, 0.775 mmol), potassium carbonate (0.446 g, 3.23 mmol) and 10 mL of DMF was stirred under nitrogen at room temperature overnight. The reaction was diluted with ethyl acetate and extracted multiple times with water and with a saturated sodium chloride solution. The organic layer was separated, dried (MgSO4), and the solvent removed under reduced pressure to give a brown oil. The oil was chromatographed on a 90 g KP-SIL 60 Δ Biotage column using 15% ethyl acetate in methylene chloride as the eluent. All fractions containing product were combined and the solvent removed under reduced pressure to give 1-phenyl-5-propyl-1H-pyrazole-4-carboxylic acid (5-bromo-6-cyanomethoxy-naphthalen-2-ylmethyl)-amide (0.196 g, 60%) as a light yellow solid, mp 175-176° C.

Provenance & Evidence