Trifluoroacetic acid → HCID 58259165, compound

Participants

Reaction Steps

In a round bottom flask, 5-amino-2-(4-methoxy-benzyl)-2H-pyrazole-3-carboxylic acid methyl ester (109, 1.4 g, 5.4 mmol) was combined with 4-fluoro-benzaldehyde (110, 0.565 mL, 5.36 mmol), trifluoroacetic acid (2.06 mL, 26.8 mmol), triethylsilane (4.28 mL, 26.8 mmol) and 50 mL of acetonitrile. The reaction was stirred at room temperature for 15 minutes, then concentrated under vacuum, combined with aqueous potassium carbonate and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The residue was recrystallized from a mixture of ethyl acetate and hexane to provide the desired compound (111, 1.6 g). 1H NMR was consistent with the compound structure.

Provenance & Evidence